Month: January 2021

61272-76-2, name is 4-Fluoro-2-iodoaniline, belongs to iodides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Safety of 4-Fluoro-2-iodoaniline

Example 26 1-Benzyl-4-(((2-(tert-butyldimethylsilyl)-5-fluoro-1H-indol-3-yl)methoxy)methyl)-N,N-dimethylcyclohexanamine (non-polar diastereomer) In a heated flask with a Schlenk attachment a mixture of Ain-04 (400 mg, 1 mmol), 4-fluoro-2-iodoaniline (Ian-04, 284 mg, 1.2 mmol), sodium carbonate (530 mg, 5 mmol) and [1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene]-(3-chloropyridyl)palladium(II) dichloride (PEPPSI, 136 mg, 0.2 mmol) was evacuated, flushed with argon and then N,N-dimethyl formamide (6 ml) was added. The reaction mixture was stirred for 20 h at 100¡ã C. and then concentrated to small volume under vacuum. Toluene was added three times to the residue, which was concentrated to dryness again each time, and then diethyl ether (30 ml) was added. The mixture was washed with water (10 ml) and the precipitated deposit was filtered off. The organic phase was washed with 1 M sodium thiosulfate solution (10 ml), sodium chloride solution (10 ml) and with water (10 ml), dried with sodium sulfate and concentrated to small volume under vacuum. The crude product (590 mg) was purified by flash chromatography (40 g, 23*2.5 cm) with methanol, purified again by flash chromatography (18 g, 18*2 cm) with chloroform/methanol (95:5) and by a further flash chromatography (20 g, 13*2.5 cm) with ethyl acetate/cyclohexane (1:2). Yield: 289 mg (57percent), yellowish solid Melting point: 58-62¡ã C. 1H-NMR (DMSO-d6): 0.35 (s, 6H); 0.85 (s, 9H); 0.87-1.00 (m, 2H); 1.13-1.35 (m, 5H); 1.77 (d, J=13.1 Hz, 2H); 2.20 (s, 6H); 2.55 (s, 2H); 3.19 (d, J=5.4 Hz, 2H); 4.51 (s, 2H); 6.92 (dt, J=9.1 Hz, 1H); 7.07-7.27 (m, 6H); 7.36 (dd, J=8.8 Hz, 1H); 10.74 (s, 1H). 13C-NMR (DMSO-d6): -5.2; 16.9; 23.9; 26.3; 31.5; 36.2; 36.5; 37.4; 57.1; 64.6; 75.2; 103.0 (d, J=23 Hz); 109.7 (d, J=27 Hz); 112.1 (d, J=11 Hz); 121.6 (d, J=5 Hz); 125.4; 127.6; 128.6; 130.5; 135.3; 136.0; 139.1; 156.7 (d, J=232 Hz).

The synthetic route of 61272-76-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUNENTHAL GMBH; US2009/215725; (2009); A1;,
Iodide – Wikipedia,
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Electric Literature of 811842-30-5, These common heterocyclic compound, 811842-30-5, name is 2-Bromo-1-fluoro-4-iodobenzene, 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.

Mix 2-bromo-1-fluoro-4-iodobenzene (18.0 g, 0.06 mol), Cu2O (36.0 mg, 0.25 mmol), and KOH (5.6 g, 0.10 mol) in 1,4-dioxane (20 ml) ), Under the protection of nitrogen, cyclopentathiol (5.1 g, 0.05 mol) was added to the system through a syringe, and the temperature was raised to 110 C. for overnight reaction. After the reaction solution was cooled to room temperature, ethyl acetate (30 ml) was added, and the filter cake was washed with ethyl acetate (20 ml). The filtrates were combined and concentrated to dryness under reduced pressure. The residue was separated by column chromatography to obtain the title compound (12.0 g, yield 72%).[1283]1H NMR (400MHz, CDCl 3) delta 7.62-7.49 (m, 1H), 7.34-7.20 (m, 1H), 7.09-6.95 (m, 1H), 3.52 (td, J = 7.2, 3.6Hz, 1H) , 2.08–1.92 (m, 2H), 1.85–1.56 (m, 6H).

The synthetic route of 811842-30-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JIANGSU HANSOH PHARMACEUTICAL GROUP CO., LTD.; SHANGHAI HANSOH BIOMEDICAL CO., LTD.; SU, Yidong; GU, Peng; CHEN, Xiaopo; LIU, Lei; BAO, Rudi; (192 pag.)WO2018/130174; (2018); A1;,
Iodide – Wikipedia,
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These common heterocyclic compound, 689291-89-2, name is 5-Bromo-2-iodobenzaldehyde, 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. Recommanded Product: 689291-89-2

To an oven-dried flask protected under a N2 atmosphere were charged compound 12 (540 mg, 1.74 mmol), trimethylsilylacetylene (0.68 g, 6.9 mmol), PdCl2(PPh3)2 (60 mg, 0.085 mmol), CuI (30 mg, 0.16 mmol), and Et3N (10 mL). The solution was bubbled by N2 at rt for 5 min and then heated to 60 C under stirring and N2 protection overnight. After the reaction was complete as checked by TLC analysis, the solvent was removed by rotary evaporation. The resulting residue was diluted with CHCl3. The mixture was filtered through a MgSO4 pad. The solution obtained was sequentially washed with HCl (aq. 10%) and brine. The organic layer was dried over MgSO4 and concentrated under vacuum to give crude 20, which was further purified by silica flash column chromatography (hexanes/CH2Cl2, 4:1) to yield compound 20 (518 mg, 1.74 mmol, 100%) as a colorless oil.

The synthetic route of 5-Bromo-2-iodobenzaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhou, Ningzhang; Wang, Li; Thompson, David W.; Zhao, Yuming; Tetrahedron; vol. 67; 1; (2011); p. 125 – 143;,
Iodide – Wikipedia,
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Electric Literature of 103440-52-4, A common heterocyclic compound, 103440-52-4, name is Methyl 2-Iodo-5-methylbenzoate, molecular formula is C9H9IO2, 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: To a solution of methyl 2-iodobenzoate (5a) (262 mg, 1.00 mmol) and benzophenone (2a)(275 mg, 1.51 mmol, 1.51 equiv) dissolved in THF (5.0 mL) was slowly added(trimethylsilyl)methylmagnesium chloride (0.983 M, THF solution, 3.05 mL, 3.00 mmol,3.00 equiv) at room temperature. After stirring for 12 h at the same temperature, to themixture was added an aqueous saturated solution of ammonium chloride (10 mL). Themixture was extracted with EtOAc (10 mL ¡Á 3), and the combined organic extract waswashed with brine (5 mL), dried (Na2SO4), and after filtration, the filtrate was concentratedunder reduced pressure. The residue was purified by flash column chromatography (silica-gel16 g, n-hexane/EtOAc = 10/1) to give 3,3-diphenyl-3H-isobenzofuran-1-one (6a) (250 mg,0.873 mmol, 87.3%) as a colorless solid.

The synthetic route of 103440-52-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nakamura, Yu; Yoshida, Suguru; Hosoya, Takamitsu; Chemistry Letters; vol. 46; 6; (2017); p. 858 – 861;,
Iodide – Wikipedia,
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Synthetic Route of 52548-14-8,Some common heterocyclic compound, 52548-14-8, name is 2-Iodo-5-methylbenzoic acid, molecular formula is C8H7IO2, 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.

1, 2, 3-Triazole (3.45 g, 50 mmol) , 2-iodo-5-methylbenzoic acid (5.24 g, 20 mmol) , cesium carbonate (11.72 g, 36 mmol) , trans-N, N’-dimethyl-1, 2-cyclohexanediamine (0.51 g, 3.60 mmol) , cuprous iodide (0.38 g, 2 mmol) and N, N-dimethylformamide (30 mL) were added sequentially to a 100 mL of single-necked round-bottomed flask under nitrogen, and the mixture was warmed gradually to 100 and reacted for 4 h. The reaction mixture was cooled, diluted with water, and extracted with ethyl acetate (200 mL x 2) . The aqueous layer was acidified to pH 12 with concentrated hydrochloric acid, and the resulting mixture was extracted with ethyl acetate (200 mL x 2) . The combined organic layers were dried over anhydrous sodium sulfate, and concentrated. The residue was purified by column chromatography on silica gel eluted with (dichloromethane/methanol (v/v) 50/1) to give the title compound (as a yellow solid, 2.76 g, 68) .[MS (ESI, neg. ion) m/z: 202.1 [M-H]- and1H NMR (CD3OD, 600 MHz) delta (ppm) : 7.88 (s, 2H) , 7.66 (d, 1H) , 7.59 (d, J 8.2 Hz, 1H) , 7.507.48 (dd, J 8.1 Hz, 1.1 Hz, 1H) , 2.45 (s, 3H) .13C NMR (CD3OD, 151 MHz) delta (ppm) : 169.8, 140.7, 137.5, 136.7, 133.5, 131.5, 129.3, 126.0, 21.0.

The synthetic route of 52548-14-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; JIN, Chuanfei; GAO, Jinheng; ZHANG, Ji; (107 pag.)WO2017/12502; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 60577-34-6,Some common heterocyclic compound, 60577-34-6, name is 4-Iodo-N-methylaniline, molecular formula is C7H8IN, 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.

7.1. Methyl 6-cyano-1-methyl-2-oxo-1,2-dihydro-4-quinolineacetate 1.1 ml of trimethylsilyl cyanide (8.4 mmol) followed by 0.15 g (0.13 mmol) of tetrakistriphenylphosphinepalladium are added to a solution of 0.50 g (1.4 mmol) of methyl 6-iodo-1-methyl-2-oxo-1,2-dihydro-4-quinolineacetate (prepared from N-methyl-4-iodoaniline according to the method described in Example 1) in 6 ml of anhydrous triethylamine. The reaction medium is then heated to reflux for 4 hours under a nitrogen atmosphere. After cooling to room temperature, the medium is poured into 60 ml of toluene and 60 ml of water. The organic phase is washed with water and the initial aqueous phase is re-extracted with dichloromethane. The organic phases are combined, dried over sodium sulphate and concentrated under vacuum. The residue is purified by flash chromatography on silica, eluding with a methanol/dichloromethane (5:95) mixture. 0.313 g of the expected nitrile is obtained. Yield=87%; Melting point=202-203 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Iodo-N-methylaniline, its application will become more common.

Reference:
Patent; SYNTHELABO; US5958924; (1999); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 17024-12-3, name is 9-Iodophenanthrene, molecular formula is C14H9I, 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. HPLC of Formula: C14H9I

Mixed under argon flow were 100 g of N,N’-diacetyl-4,4′-benzidine (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 337 g of 9-iodophenanthrene, 204 g of anhydrous potassium carbonate (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 4.7 g of copper powder (manufactured by Hiroshima Wako Co., Ltd.) and 750 ml of decalin, and they were reacted at 190C for 3 days. After cooling, 2 liter of toluene was added thereto to filter an insoluble matter. The matter filtered was dissolved in 4.5 liter of chloroform to filter off an insoluble matter, and then the filtrate was treated with activated carbon and concentrated under reduced pressure. Acetone 3 litter was added when the solution became slurry in the middle of concentration, and crystal deposited was filtered and dried. This was suspended in a mixture of 2 liter of ethylene glycol and 20 ml of water, and 110 g of a 85 % potassium hydroxide aqueous solution was added thereto, followed by carrying out reaction at 120C for 12 hours. After left cooling down to a room temperature, the reaction liquid was injected to 4 liter of water and treated with activated carbon, and then it was concentrated under reduced pressure. Acetone was added when the solution became slurry, and crystal deposited was filtered and dried to obtain 116 g of N,N’-bis(phenantho-9-yl)-4,4′-benzidine (A3).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 17024-12-3, its application will become more common.

Reference:
Patent; IDEMITSU KOSAN CO., LTD.; EP1559706; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 202982-67-0, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 202982-67-0, name is 4-Chloro-3-fluoroiodobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

a) (4-Chloro-3-fluoro-phenyl)-propynoic acid ethyl ester (Vd) Under argon atmosphere, a four neck flask was charged with 1-chloro-2-fluoro-4-iodo-benzene (50.5 g, 0.20 mol), bis(triphenylphosphine) palladium(II) chloride (2.76 g, 3.94 mmol, 2 mol %), copper(I) iodide (1.50 g, 7.80 mol, 4 mol %) and dry THF (600 ml). At r.t., cesium carbonate (128.3 g, 0.39 mol, 2 eq.) was added over 5 min. Finally, propynoic acid ethyl ester (38.6 g, 0.39 mol, 2 eq.) was added, and the reaction was stirred for 48 h at 35 C. The reaction mixture was evaporated to dryness, and the residue was taken up in toluene (50 ml) and heptane (100 ml). The resulting suspension was stirred at 40 C. for 1 h and filtered afterward over celite. The filtrate was concentrated, and the product was purified by silica gel filtration (toluene/heptane 1:2) to yield 38.8 g (87%) of the Vd as a light yellow solid. ES-MS m/e: 227.2 (M-H+).

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-Chloro-3-fluoroiodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hoffmann-Emery, Fabienne; Puentener, Kurt; Ratni, Hasane; US2010/152462; (2010); A1;,
Iodide – Wikipedia,
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Application of 19230-28-5, A common heterocyclic compound, 19230-28-5, name is 1,3-Dichloro-2-iodobenzene, molecular formula is C6H3Cl2I, 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: (S)-3-((R)-Hydroxyphenylmethyl)pyrrolidine-1-carboxylic acid t-butyl ester 11a (250 mg, 0.9 mmol), copper(I) iodide (51 mg, 270 mumol), 1,10-phenanthroline (97 mg, 540 mumol) and 2,4-difluoro-1-iodobenzene (216 muL, 1.8 mmol) were combined in a vial under air. Toluene (1.4 mL, 14 mmol) was added, followed by the addition of cesium carbonate (587 mg, 1.8 mmol). Air was bubbled through the mixture, the vial was sealed, and the mixture was heated at 105C for 48 hours. The mixture was filtered through Celite. The Celite was then rinsed with DCM (2 x 15 ml), and the resultant filtrate was concentrated. The resultant oil was treated with 1.25 M of HCl in EtOH (5.8 mL, 7.2 mmol) and stirred overnight. The mixture was concentrated and purified by reverse phase preparative HPLC (10 to 70% CH3CN in water with 0.5% TFA) to yield 76 mg (97% purity, 26% yield) of the title compound as the mono-TFA salt.

The synthetic route of 19230-28-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Van Orden, Lori Jean; Van Dyke, Priscilla M.; Saito, D. Roland; Church, Timothy J.; Chang, Ray; Smith, Jacqueline A.M.; Martin, William J.; Jaw-Tsai, Sarah; Stangeland, Eric L.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 5; (2013); p. 1456 – 1461;,
Iodide – Wikipedia,
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Related Products of 20555-91-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 20555-91-3, name is 1,2-Dichloro-4-iodobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 1.00 mmol arylhalide, 1.30 mmol furfural-boronic acid and 0.05 mmolBis(triphenylphosphine)palladium(II) dichloride were treated with 0.30 mLdimethoxyethane, 0.50 mL ethanol and 0.30 mL aqueous 2M sodium carbonate solution.The reaction was heated to 65C for 1h or until the TLC showed no remaining startingmaterial. The mixture was evaporated and extracted three times with ethyl acetate. Thecombined organic layers were washed with brine, dried over MgSO4, filtered andconcentrated. The crude product was purified by column chromatography usinghexanes/ethyl acetate (9:1).

The synthetic route of 1,2-Dichloro-4-iodobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Krake, Susann H.; Martinez, Pablo David G.; McLaren, Jenna; Ryan, Eileen; Chen, Gong; White, Karen; Charman, Susan A.; Campbell, Simon; Willis, Paul; Dias, Luiz Carlos; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 929 – 936;,
Iodide – Wikipedia,
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