Month: October 2020

Adding some certain compound to certain chemical reactions, such as: 20555-91-3, name is 1,2-Dichloro-4-iodobenzene, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 20555-91-3. 20555-91-3

General procedure: To a stirred solution of but-3-yn-2-amine (¡À) (Intermediate 2a) (5.00g, 72.34mmol) in dichloromethane (100 mL), tert-butyl 4-(chlorocarbonyl) piperazine-l-carboxylate (Intermediate 5) (17.90 g, 72.34mmol) and DIPEA (37.60 mL, 217 mmol) were added at RT. The reaction mixture, after being stirred at RT for 16 h, washed with saturated NaHC03 solution and brine. The dichloromethane layer was collected, dried and concentrated. The crude obtained was purified by Combiflash on silica gel (hexanes/ethyl acetate=65/35) to get the title compound (8.00 g, 39.4%). LCMS: m/z = 282.2 [M+H]+.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1,2-Dichloro-4-iodobenzene.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; CHIKKANNA, Dinesh; KHAIRNAR, Vinayak V.; RAMACHANDRA, Muralidhara; SATYAM, Leena Khare; (139 pag.)WO2019/142126; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

The chemical industry reduces the impact on the environment during synthesis 54811-38-0, name is 5-Iodo-2-methylbenzoic acid, I believe this compound will play a more active role in future production and life. 54811-38-0

To a solution of compound 6 (40.0 g, 0.153 mol) in MeOH (400 mL) was added dropwise a freshly prepared solution of SOCI2 (22 mL, 0.305 mol) in MeOH (400 mL) at O0C. The mixture was heated to reflux for 4 hours. TLC (petroleum ether: ethyl acetate = 10:1) showed the reaction was complete, then the mixture was concentrated in vacuo. The residue was desolved in ethyl acetate (800 mL) and washed with water (200 mLx2), saturated aqueous sodium carbonate (200 mLx2) and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give compound 7 as a yellow solid. 1H NMR (300 MHz, CDCI3): delta 8.21 (S, 1 H), 7.67-7.70 (dd, J = 9.0 Hz, 1 H), 6.97-6.99 (d, J = 6.0 Hz, 1 H), 3.88 (s, 3H), 2.53 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis 54811-38-0. I believe this compound will play a more active role in future production and life.

Reference:
Patent; PFIZER INC.; WO2006/117669; (2006); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

364-12-5, The chemical industry reduces the impact on the environment during synthesis 364-12-5, name is 5-Bromo-2-iodobenzotrifluoride, I believe this compound will play a more active role in future production and life.

(1) Synthesis of 1-[4-bromo-2-(trifluoromethyl)phenyl]cyclobutanol To a solution of 5-bromo-2-iodobenzotrifluoride (5.00 g) in dehydrated tetrahydrofuran (140 mL), n-butyl lithium (2.69 mol/L, solution in n-hexane, 5.30 mL) was added at -78C and the mixture was stirred at that temperature for 25 minutes. After adding a solution of cyclobutanone (999 mg) in tetrahydrofuran (5.00 mL), the mixture was brought to room temperature and stirred for 3 days. After adding a saturated aqueous solution of ammonium chloride under cooling with ice, two extractions were conducted with ethyl acetate. The combined organic layers were washed with water and thereafter dried over anhydrous magnesium sulfate. After removing the desiccant by filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate = 98:2-80:20) to give 1-[4-bromo-2-(trifluoromethyl)phenyl]cyclobutanol as a pale yellow oil (3.00 g). 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 1.71 – 1.88 (m, 1 H) 2.20 – 2.49 (m, 3 H) 2.52 – 2.70 (m, 2 H) 7.29 – 7.35 (m, 1 H) 7.62 – 7.69 (m, 1 H) 7.78 – 7.84 (m, 1 H). MS EI posi: 294[M]+.

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-2-iodobenzotrifluoride. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Taisho Pharmaceutical Co., Ltd.; TAKAYAMA, Tetsuo; SHIBATA, Tsuyoshi; SHIOZAWA, Fumiyasu; KAWABE, Kenichi; SHIMIZU, Yuki; HAMADA, Makoto; HIRATATE, Akira; TAKAHASHI, Masato; USHIYAMA, Fumihito; OI, Takahiro; SHIRASAKI, Yoshihisa; MATSUDA, Daisuke; KOIZUMI, Chie; KATO, Sota; EP2881384; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

455-13-0, Adding a certain compound to certain chemical reactions, such as: 455-13-0, name is 4-Iodobenzotrifluoride, belongs to iodides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 455-13-0.

General procedure: To a stirred solution of aryl halides (2.0 mmol) and thiourea (1.2 equiv) in dry DMSO (2.0 mL) at rt was added nano CuO (5.0 mol %) followed by Cs2CO3 (2.0 equiv) and heated at 110 C for 15 h. The progress of the reaction was monitored by TLC. After the reaction was complete, the reaction mixture was allowed to cool, and a 1:1 mixture of ethyl acetate/water (20 mL) was added. The combined organic extracts were dried with anhydrous Na2SO4. The solvent and volatiles were completely removed under vacuum to give the crude product, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 9:1) to afford the corresponding coupling product in excellent yields.Recycling of the catalyst:after the reaction was complete, the reaction mixture was allowed to cool, and a 1:1 mixture of ethyl acetate/water (2.0 mL) was added and CuO was removed by centrifugation. After each cycle, the catalyst was recovered by simple centrifugation, washing with deionized water and ethyl acetate and then drying in vacuo. The recovered nano CuO was used directly in the next cycle.Data of representative examples:Dip-tolylsulfane (Table 3, entry 3): yellow oil;1H NMR (200 MHz, CDCl3, TMS): delta = 7.21 (d, 4H, J = 8.0 Hz), 7.06 (d, 4H, J = 8.0 Hz), 2.32 (s, 6H); 13C NMR (50 MHz, CDCl3, TMS): delta = 136.7, 132.81, 131.0, 129.8, 96.1.Table 3, entry 3): yellow oil;1H NMR (200 MHz, CDCl3, TMS): delta = 7.21 (d, 4H, J = 8.0 Hz), 7.06 (d, 4H, J = 8.0 Hz), 2.32 (s, 6H); 13C NMR (50 MHz, CDCl3, TMS): delta = 136.7, 132.81, 131.0, 129.8, 96.1.Bis(4-ethylphenyl)sulfane (Table 3, entry 4): colorless oil; 1HNMR (300 MHz, CDCl3, TMS): delta = 7.21(d, 4H, J = 7.8 Hz), 7.07 (d, 4H, J = 7.8 Hz), 2.62-2.52 (m, 4H), 1.26 (t, 6H, J = 7.8 Hz);13C NMR (75 MHz, CDCl3, TMS): delta = 143.1, 132.7, 131.0, 128.6, 28.3, 15.4; mass (EI): m/z 242 [M]+; Anal. calcd for: (C16H18S) C, 79.29; H, 7.49; S, 13.23; found: C,79.22; H,7.42; S,13.19.Table 3, entry 4): colorless oil; 1HNMR (300 MHz, CDCl3, TMS): delta = 7.21(d, 4H, J = 7.8 Hz), 7.07 (d, 4H, J = 7.8 Hz), 2.62-2.52 (m, 4H), 1.26 (t, 6H, J = 7.8 Hz);13C NMR (75 MHz, CDCl3, TMS): delta = 143.1, 132.7, 131.0, 128.6, 28.3, 15.4; mass (EI): m/z 242 [M]+; Anal. calcd for: (C16H18S) C, 79.29; H, 7.49; S, 13.23; found: C,79.22; H,7.42; S,13.19.Bis(3-nitrophenyl)sulfane (Table 3, entry 7): pale yellow oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 8.19-8.15 (m, 4H), 7.65 (d, 2H, J = 8.3 Hz), 7.55 (t, 2H, J = 8.3 Hz); 13C NMR (75 MHz, CDCl3, TMS): delta = 148.8, 136.7, 130.7, 125.6, 122.7; mass (EI): m/z 276 [M]+; Anal. calcd for: (C12H8N2O4S) C, 52.17; H, 2.92; S, 11.61; N, 10.14; found: C, 52.12; H, 2.86; S, 11.55; N, 10.9.Table 3, entry 7): pale yellow oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 8.19-8.15 (m, 4H), 7.65 (d, 2H, J = 8.3 Hz), 7.55 (t, 2H, J = 8.3 Hz); 13C NMR (75 MHz, CDCl3, TMS): delta = 148.8, 136.7, 130.7, 125.6, 122.7; mass (EI): m/z 276 [M]+; Anal. calcd for: (C12H8N2O4S) C, 52.17; H, 2.92; S, 11.61; N, 10.14; found: C, 52.12; H, 2.86; S, 11.55; N, 10.9.4,4′-Thiodianiline (Table 3, entry 11): brown solid; mp 104-105 C; 1H NMR (300 MHz, CDCl3, TMS): delta = 7.10 (d, 4H, J = 8.68 Hz), 6.52 (d, 4H, J = 8.68 Hz), 3.51 (br s, 4H); 13C NMR (75 MHz, CDCl3, TMS): delta = 145.5, 133.8, 132.6, 124.8, 115.6; mass (EI): m/z 216 [M]+; Anal. calcd for: (C12H12N2S) C, 66.63; H, 5.59; N, 12.95; S, 14.82; Found: C, 66.61; H, 5.58; N, 12.92; S, 14.81.Table 3, entry 11): brown solid; mp 104-105 C; 1H NMR (300 MHz, CDCl3, TMS): delta = 7.10 (d, 4H, J = 8.68 Hz), 6.52 (d, 4H, J = 8.68 Hz), 3.51 (br s, 4H); 13C NMR (75 MHz, CDCl3, TMS): delta = 145.5, 133.8, 132.6, 124.8, 115.6; mass (EI): m/z 216 [M]+; Anal. calcd for: (C12H12N2S) C, 66.63; H, 5.59; N, 12.95; S, 14.82; Found: C, 66.61; H, 5.58; N, 12.92; S, 14.81.Dithiophen-3-ylsulfane (Table 3, entry 15): yellow oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 7.31-7.25 (m, 2H), 7.17-7.11(m, 2H), 6.96-6.94 (m, 2H); 13C NMR (75 MHz, CDCl3, TMS): delta = 129.6, 126.4, 124.7; mass (EI): m/z 197 [M]+; Anal. calcd for: (C8H6S3) C, 48.45; H, 3.05; S, 48.50; found: C,48.42; H,3.02; S,48.47.Table 3, entry 15): yellow oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 7.31-7.25 (m, 2H), 7.17-7.11(m, 2H), 6.96-6.94 (m, 2H); 13C NMR (75 MHz, CDCl3, TMS): delta = 129.6, 126.4, 124.7; mass (EI): m/z 197 [M]+; Anal. calcd for: (C8H6S3) C, 48.45; H, 3.05; S, 48.50; found: C,48.42; H,3.02; S,48.47.Dipyrimidin-5-ylsulfane (Table 3, entry 17): colorless oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 9.15 (s, 2H), 8.74(s, 4H); 13C NMR (75 MHz, CDCl3, TMS): delta = 158.6, 157.7, 129.8; mass (EI): m/z 190 [M]+; Anal. calcd for: (C8H6N4S) C, 50.51; H, 3.18; N, 29.45; S, 16.86; found: C, 50.45; H, 3.13; N, 29.41; S, 16.81.Table 3, entry 17): colorless oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 9.15 (s, 2H), 8.74(s, 4H); 13C NMR (75 MHz, CDCl3, TMS): delta = 158.6, 157.7, 129.8; mass (EI): m/z 190 [M]+; Anal. calcd for: (C8H6N4S) C, 50.51; H, 3.18; N, 29.45; S, 16.86; f…

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Iodobenzotrifluoride, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Reddy, K. Harsha Vardhan; Reddy, V. Prakash; Shankar; Madhav; Anil Kumar; Nageswar; Tetrahedron Letters; vol. 52; 21; (2011); p. 2679 – 2682;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

1450754-38-7, These common heterocyclic compound, 1450754-38-7, name is 3-(But-3-yn-1-yl)-3-(2-iodoethyl)-3H-diazirine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

(g) Compound 6 (400 mg, 1.6 mmol, 1.0 eq), sodium azide (125 mg, 1.92 mmol, 1.2 eq) and DMF (4 ml) were added to a reaction flask, and the temperature was raised to 70 C, and the reaction was carried out for 5 hours in the dark;Quenched with water, extracted with ethyl acetate, dried and dried to give a crude200 mg of compound 7, yield: 76%.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1450754-38-7.

Reference:
Patent; Suzhouguangdian Biological Technology Co., Ltd.; Ni Runyan; Wang Wei; (8 pag.)CN109369532; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

83171-49-7, A common heterocyclic compound, 83171-49-7, name is 3-Chloro-5-iodoaniline, molecular formula is C6H5ClIN, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: The corresponding pyrazinoic acid (5.0 mmol) was dispersed in dry toluene (20 mL) and mixed with 1.5eq. of thionyl chloride (0.55 mL, 7.5 mmol). The reaction mixture was heated to reflux for approximately 1 h. Next, the excess of thionyl chloride was removed by repeated evaporation with dry toluene under vacuum.The crude acyl chloride was dissolved in dry acetone(20 mL) and added drop-wise to a stirred solution of the corresponding aniline (5.0 mmol) with triethylamine(5.0 mmol) in dry acetone (30 mL). The reaction mixture was stirred at ambient temperature for up to 6 h. The completion of the reaction was monitored by TLC (eluent: hexane/ethyl acetate; r =2 : 1). The crude product adsorbed on silica gel by solvent evaporation was purified by flash chromatography(hexane/ethyl acetate gradient elution).The analytical data of the prepared compounds were fully consistent with the proposed structures and are available in the Supplementary Data.

The synthetic route of 83171-49-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zitko, Jan; Barbora, Servusova-Vanaskova; Paterova, Pavla; Navratilova, Lucie; Trejtnar, Frantisek; Kunes, Jiri; Dolezal, Martin; Chemical Papers; vol. 70; 5; (2016); p. 649 – 657;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

444-29-1, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 444-29-1, name is 1-Iodo-2-(trifluoromethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of [9-((1R,2R,4R,5R)-4-ethynyl-7,7-dimethyl-3,6,8-trioxabicyclo[3.3.0]oct-2-yl)purin-6-yl]cyclopentylamine (40 mg, 0.12 mmol), a compound of formula (5), in tetrahydrofuran (4 ml) under nitrogen was added catalytic amounts (3 mg) of dichlorobis(triphenylphosphine)palladium(II) and copper(II)iodide, followed by 1-iodo-2-trifluoromethylbenzene (0.25 ml, 0.3 mmol). Triethylamine (0.4 ml) was then added, and the mixture stirred for 15 minutes at room temperature. The solvent was removed under reduced pressure, and the residue was purified by preparative TLC, eluding with methanol:methylene chloride (6.5:1), to yield [9-((1R,2R,4R,5R)-7,7-dimethyl-4-{2-[2-(trifluoromethyl)-phenyl]ethynyl}-3,6,8-trioxabicyclo[3.3.0]oct-2-yl)purin-6-yl]cyclopentylamine, a compound of formula (6).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Zablocki, Jeff; Palle, Venkata; Elzein, Elfatih; Li, Xiaofen; US2004/43960; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

1450754-38-7, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 1450754-38-7, name is 3-(But-3-yn-1-yl)-3-(2-iodoethyl)-3H-diazirine, A new synthetic method of this compound is introduced below.

A mixture of compound S9 (38.1 mg, 167 tmo1, I equiv) and iodo-diazirine 57 (41.4 mg, 178 p.moi, 1.00 equiv) was dissolved in DMF (1.7 rnL) at 24 C. Potassium carbonate (46.1 rng, 334 imol, 2.00 equiv) was added to the resulting mixture. The reaction mixture was stirred for 12 hours at 50 C, then cooled for 30 minutes to 24 C and partitioned between ethyl acetate (5 mL) and Di water (5 mL). The organic portion was separated and washed with brine (3 x 5 mL). The organic portion was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford an off white powder. The powder was purified by flash column chromatography (20% ethyl acetate-hexanes) to afford the celecoxib analog 9 as a pale yellow oil (39.4 mg, 68%).R= 0.58 (20% ethyl acetate-hexanes; UV). ?HNIvR (500 MHz, CDCI3): d 7.74 (d, 2H, J 7,6 Hz, El3). 7.48 (dd, 2H, J == 7.6, 7.6 Hz, H4), 7.36 (t, IH, J == 7.6, 7.6 Hz, H5), 5.92 (s, IH, Hi), 3.99 (t, 2H, J = 6.0 Hz, H2), 2.01-195 (m, 5H, Ho/HfHc), 1.66 (t, 2H, J = 6.8 Hz, FL). ?3C NMR (125 MHz, CDC13): oe 154.0 (C), 141.8 (q, 2JCF 38.4 Hz, CT:1), 137.5 (C), 129.0 (CH), 127.7 (CH). 123.0 (CH), 120.9 (q, IJCF = 267.3 Hz CF3), 84.7 (q, 3JCF = 2. 1 Hz, CH), 82.4 (C), 69.4 (CH), 67.1 (OCH2), 32.6 (CFL), 32.3 (Cl-i2), 26.1 (CN2), 13.2 (CH3). ?9F NMR (375 MHz, CDCI3): oe -63.3 ppm. [R (ATR-FTIR). cnf?: 3303 (s), 1594 (m). 1562(m), 1508 (rn), 1488 (m), 1457 (m), 1243 (s), 1126 (s), 1099 (s), 968 (s), 759 (s), 639 (s) cm- 1. HRMS-ESI (m/z): [MH-+1j calculated ?for Cv7HT6F3N4O. 34g. 1271; found, 349.1276.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; WOO, Christina, M.; GAO, Jinxu; (555 pag.)WO2018/226828; (2018); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

460-37-7,Some common heterocyclic compound, 460-37-7, name is 1,1,1-Trifluoro-3-iodopropane, molecular formula is C3H4F3I, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

28.4 g of 4,6-diamino-2-mercaptopyrimidine (SM) was weighed and dissolved in 100 mL of N,N-dimethylformamide.Then add 82.8 g of potassium carbonate to the system.Trifluoromethyl-iodopropane was added 179.2g,The reaction was carried out for 6 h under the conditions of a 130 C oil bath.The mixture was cooled to room temperature, and the mixture was combined with EtOAc.Recrystallization from methylene chloride gave 38.1 g of a yellow solid 2-[(3,3,3-trifluoropropyl)thio]pyrimidine-4,,6-diamino (intermediate 1),The yield was 80%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,1,1-Trifluoro-3-iodopropane, its application will become more common.

Reference:
Patent; Changzhi Yuan Yan Pharmaceutical Technology Co., Ltd.; Zhou Jian; Cai Kun; (13 pag.)CN108440627; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

289039-29-8, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 289039-29-8, name is 2-Chloro-5-iodobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

In a sealed tube, a mixture of 2-chloro-5-iodobenonitrile 111-5 (1.30 g, 5 mmol), 0.5 M (2-tert-butoxy-2-oxoethyl) zinc(II) chloride 111-6 in ether (11 mL, 5.5 mmol), Pd(dba)2 (144 mg, 0.25 mmol), Q-phos (178 mg, 0.25 mmol), and THF (20 mL) under argon was stirred at 70 C for 18 hours. After cooling to room temperature, the solvents were evaporated and the residue was redissolved in ethyl acetate, washed with water and brine, dried over Na2SO4 and concentrated to dryness by rotary evaporation. The crude product was purified by silica gel flash chromatography, eluted with 30% ethyl acetate in hexane to give tert-butyl 2- (4-chloro-3-cyanophenyl)acetate 111-7 as a brown oil. MS m/z 252.1 (M + 1).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; IRM LLC; CHENG, Dai; ZHANG, Guobao; HAN, Dong; GAO, Wenqi; PAN, Shifeng; WO2010/101849; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com