Category: 77317-55-6

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. 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H8INO2

A solution of methyl 2-amino-5-iodobenzoate (7.02 g, 25.3 mmol) and 2-(tetrahydro-2H-pyran-4-yl)acetic acid (3.76 g, 26.1 mmol) in pyridine (25 mL) was stirred at ?-40 C. under argon while POCl3 (2.58 g, 27.8 mmol) was added dropwise over 3 minutes. The cold bath was immediately removed and the reaction was allowed to stir for 1 hour. The reaction was then diluted with water (75 mL) and extracted with DCM (75 mL). The combined orange organic layers were washed with 6 M aqueous HCl (50 mL), 1 M aqueous HCl (50 mL), and 2 M aqueous K3PO4 (50 mL), dried (Na2SO4), filtered, and concentrated to provide the title compound as an orange solid.

According to the analysis of related databases, 77317-55-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JOHNSON & JOHNSON; LEONARD, KRISTI A.; BARBAY, KENT; EDWARDS, JAMES P.; KREUTTER, KEVIN D.; KUMMER, DAVID A.; MAHAROOF, UMAR; NISHIMURA, RACHEL; URBANSKI, MAUD; VENKATESAN, HARIHARAN; WANG, AIHUA; WOLIN, RONALD L.; WOODS, CRAIG R.; FOURIE, ANNE; XUE, XIAOHUA; CUMMINGS, MAXWELL D.; MCCLURE, KELLY; TANIS, VIRGINIA; US2015/111870; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

77317-55-6, name is Methyl 2-amino-5-iodobenzoate, 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. Recommanded Product: Methyl 2-amino-5-iodobenzoate

Methyl anthranilate (15) (2.0 g, 13.2 mmol), granulatediodine (3.36 g, 13.2 mmol) and hydrogen peroxide-urea(1.24 g, 13.2 mmol), were dissolved in 20 mL of ethylacetate. The reaction mixture was stirred for 1.5 h at roomtemperature and then washed with sodium thiosulfate(3 × 10 mL) and water (3 × 10 mL); then solvent wasevaporated under reduced pressure to afford methyl2-amino-5-iodobenzoate (16) as a brown solid (3.33 g,yield 91%). The solid was hydrolyzed using NaOH/MeOH(5%) to give 2-amino-5-iodobenzoic acid (17) (2.81 g, yield89%). Finally, the acid was cyclized with triphosgene andtriethylamine as base affording 6-iodoisatoic anhydride(6-iodo-1H-benzo[d][1,3]oxazine-2,4-dione, 2) with a76% yield (2.34 g).

The synthetic route of 77317-55-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; De La Cruz, Armando; Vega-Acevedo, Carlos Alejandro; Rivero, Ignacio A.; Chavez, Daniel; Journal of the Brazilian Chemical Society; vol. 29; 8; (2018); p. 1607 – 1611;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 77317-55-6, 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. 77317-55-6, name is Methyl 2-amino-5-iodobenzoate belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Phosphorus oxychloride (1.47 g, 9.6 mmol, 0.9 mL) was added dropwise at -10 C to a stirred pyridine (40 mL) solution of N-Boc-L-proline 7 (1.74 g, 8.08 mmol) and arylamine 6 (2.24 g, 8.08 mmol) under argon atmosphere. The reaction mixture was stirred for 30 min (-10-5 C), then poured into water (200 mL) containing ice, and extracted with EtOAc. The aqueous layer was additionally extracted with EtOAc. The extract was washed with water, saturated NaHCO3 solution, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel using CHCl3 as the eluent. The isolated product with Rf 0.56 (EtOAc/LP, 1 : 2) was crystallized from petroleum ether to give amide 8 (2.8 g, 74%) as light brown crystals, m.p. 92-95 C, [alpha]23D -103.96 (c = 1.0, CHCl3). 1H NMR (CDCl3), delta: 1.35 and 1.49 (both br.s, integral ratio of 5/4, 9 H, Me3C); 1.74-2.42 (m, 4 H, HC(4), HC(5)); 3.39-3.80 (m, 2 H, HC(3)); 3.91 (s, 3 H, MeO); 4.27 and 4.41 (both m, integral ratio of 5/4, 1 H, HC(1)); 7.81 (br.d, 1 H, HC(3), J = 8.2 Hz); 8.34 (br.s, 1 H, HC(4)); 8.57 (br.d, 1 H, HC(6), J = 8.2 Hz); 11.43 (m, 1 H, HN) (mixture of rotamers, see Ref. 21).

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, Methyl 2-amino-5-iodobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Lozanova; Stepanov; Mel?nik; Zlokazov; Veselovsky; Russian Chemical Bulletin; vol. 68; 1; (2019); p. 64 – 67; Izv. Akad. Nauk, Ser. Khim.; 1; (2019); p. 64 – 67,4;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 77317-55-6, These common heterocyclic compound, 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, 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.

Methyl 2-amino-5-(phenethylthio)benzoate (2) Synthesized using reported procedure with modification (see, e.g., Itoh, T; Mase, T. Org. Lett. 2004, 6, 4587-4590). To a round-bottom-flask under nitrogen were added methyl 2- amino-5-iodobenzoate (1) (831 mg, 3 mmol, 1.0 equiv.), z-P^Net (775 mg, 1.05 mL, 6 mmol, 2.0 equiv.) and dry 1,4-dioxane (30 mL). Catalyst Pd2(dba)3 (137 mg, 0.15 mmol, 0.05 equiv.), Xantphos (173 mg, 0.3 mmol, 0.1 equiv.) were then added and the mixture were stirred for 15 minutes. 2-Phenylethanethiol (415 mg, 0.4 mL, 3 mmol, 1.0 equiv.) was added and then the mixture was heated to reflux for 16 hours. The reaction mixture was then allowed to cool down to room temperature. The reaction mixture was then filtered and concentrated under reduced pressure. The crude product was purified by flash column chromatography (ethyl acetate_hexanes=15:85) on silica gel to afford 2 (862 mg, 82%) as yellow oil which solidified upon standing. XH NMR (300 MHz, CDC13) delta 7.99 (s, 1H), 7.37-7.14 (m, 6H), 6.62 (d, J= 6.0 Hz, 1H), 5.80 (s, 2H), 3.87 (s, 3H), 3.04-2.99 (m, 2H), 2.87-2.82 (m, 2H); 1 C NMR (75 MHz, CDC13) delta 168.01, 149.86, 140.36, 138.81, 135.95, 128.50, 128.41, 126.28, 120.81, 117.42, 111.11, 51.64, 37.81, 35.94.

The synthetic route of 77317-55-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; NIKOLOVSKA-COLESKA, Zaneta; STUCKEY, Jeanne A.; MADY, Ahmed; MIAO, Lei; (140 pag.)WO2016/172218; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: Methyl 2-amino-5-iodobenzoate

methyl 4-amino-4′-propyl-[l,l’-biphenyl]-3-carboxylate (4a) Synthesized using reported procedure with modification (US Patent Application Publication Culshaw et al, Pub. No. US 2008/0293939 Al, Nov 27, 2008). To a round-bottom-flask under nitrogen methyl 2-amino-5-iodobenzoate (1) (831 mg, 3 mmol, 1.0 equiv.), 4- propylphenylboronic acid (541 mg, 3.3 mmol, 1.1 equiv.) and DMF (20 mL) were added, followed by addition of catalyst Pd(dppf)Cl2 (110 mg, 0.15 mmol, 0.05 equiv.) and the mixture were stirred for 15 minutes. 2M Na2CC>3 solution (7.5 mL, 15 mmol, 5.0 equiv.) was added and then the mixture was heated at 80 C for 16 hours. The reaction mixture was allowed to cool down to room temperature. The reaction mixture was filtered and concentrated under reduced pressure. H20 (20 mL) was added to the residue which was extracted with EtOAc (2 x 20 mL). All the organic extracts were combined, dried over NaSC>4 and concentrated under reduced pressure. The crude product was purified by flash column chromatography (ethyl acetate_hexanes=20:80) on silica gel to afford 4a (418 mg, 51%) as yellow solid. XH NMR (400 MHz, CDCI3) delta 8.11 (s, 1H), 7.53-7.20 (m, 5H), 6.71 (d, J= 8.0 Hz, 1H), 5.74 (s, 2H), 3.88 (s, 3H), 2.60 (t, J= 8.0 Hz, 2H), 1.71-1.61 (m, 2H), 0.96 (t, J = 8.0 Hz, 3H); 1 C NMR (100 MHz, CDCI3) delta 168.56, 149.48, 140.96, 137.74, 132.70, 129.37, 129.23, 128.81, 126.03, 117.13, 110.90, 51.54, 37.61, 24.55, 13.82.

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 77317-55-6.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; NIKOLOVSKA-COLESKA, Zaneta; STUCKEY, Jeanne A.; MADY, Ahmed; MIAO, Lei; (140 pag.)WO2016/172218; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Methyl 2-amino-5-iodobenzoate

EXAMPLE 1002-(4-((2-Chlorothiophene-5-carboxamido)methyl)-lH-l,2,3-triazol-l-yl)-5-(2-oxopyridin- l(2H)-yl)benzoic acid (100); SCHEME 9Step 1 : Methyl 2-amino-5-iodonezoate (3.00 g, 10.8 mmol) was stirred in 35 rnL TFA in ice bath. To it was added sodium nitrite (820 mg, 12 mmol) in small portions. The mixture was stirred in ice bath for 40 min. To it was added an ice-cold solution of sodium azide (1.41 g, 21.6 mmol) in 8 mL water. The mixture was stirred for 3 hrs, diluted with ethyl acetate (500 mL), washed with brine three times, dried, and concentrated in vacuo to give compound 9.2 in quantitative yield.

According to the analysis of related databases, 77317-55-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; SCARBOROUGH, Carroll; WO2008/86226; (2008); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, 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. Computed Properties of C8H8INO2

(E)-3-(Naphthalen-2-yl)but-2-enoic acid (1.00 g, 4.71 mmol) was suspended in dry dichloromethane (15 mL) in a flame dried flask under an argon atmosphere and cooled to 0 C. Oxalyl chloride (0.848 g, 0.447 mL, 9.42 mmol) and a catalytic amount of DMF (2 drops) was added to the suspension and allowed to warm to room temperature. The solution was stirred at room temperature for 5 h after which all volatiles were removed under reduced pressure. The crude product was redissolved in dry dichloromethane (15 mL) and solvent removed under reduced pressure three times before drying under high vac. The crude product was redissolved in dry THF (20 mL) in a flame-dried flask under an argon atmosphere. To this was added 5-iodo-2-aminobenzoate (1.86 g, 7.07 mmol), pyridine (1.12 g, 1.14 mL, 14.1 mmol) and a catalytic amount of DMAP (0.01 g, 0.082 mmol). After stirring at 60 C for 16 h, the reaction was allowed to cool to room temperature, poured onto 1 N HCl and extracted into diethyl ether. The combined organic layers were dried over anhydrous magnesium sulphate and concentrated under vacuum to give the crude product.Purification by flash chromatography (8% methanolin dichloromethane) afforded the analytically pure product. (Yield:1.60 g, 3.39 mmol, 72%).1H NMR (CDCl3, 500 MHz, 20 C): delta =11.18(s, 1H, NH), 8.70 (d, J = 9.1 Hz, 1H, ArH), 8.36 (d, J = 2.2 Hz, 1H, ArH),7.98 (d, J = 1.3 Hz, 1H, NpH), 7.89 (m, 3H, ArH NpH), 7.83 (d,J = 2.2 Hz, 1H, NpH), 7.64 (dd, J = 8.5, 1.9 Hz, 1H, NpH), 7.53 (m, 2H,NpH), 6.37 (q, J = 0.9 Hz, 1H, COCH), 3.95 (s, 3H, COOCH3), 2.77 (d,J = 1.0 Hz, 3H, CCH3). 13C NMR (CDCl3, 125 MHz, 20 C): delta =167.6,165.3,154.0,143.1,141.7,139.6,139.3,133.4,133.1,128.5,128.2,127.6,126.6, 126.5, 125.8, 124.0, 122.2, 120.8, 116.5, 84.7, 52.6, 18.0. ESMScalcd for C22H18INNaO3 [M+Na]+: 494.0224, found 494.0221. HPLC(method A): Rt = 14.14 min.

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

Reference:
Article; Waghorn, Philip A.; Jackson, Mark R.; Gouverneur, Veronique; Vallis, Katherine A.; European Journal of Medicinal Chemistry; vol. 125; (2017); p. 117 – 129;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 77317-55-6, 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. 77317-55-6, name is Methyl 2-amino-5-iodobenzoate belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of CuI (110 mg, 0.58 mmol), Pd(OAc)2 (60 mg, 0.27 mmol), and Ph3P (130 mg, 0.49 mmol) in MeCN (30 mL) deaerated (UST) under argon atmosphere was stirred at 20 C for 20 min. Iodide 6 (1.39 g, 5.0 mmol), Et3N (1.53 g, 15.11 mmol, 2.1 mL), H2O (0.15 g, 8.33 mmol), and finely ground CaC2 (1.0 g, 15.60 mmol) were then added. The reaction mixture was stirred for 7 h and concentrated in vacuo; the residue was extracted with hot EtOAc. The extract was filtered and concentrated in vacuo, the residue was purified by chromatography on SiO2 using gradient elution of PhH -> PhH/EtOAc (4 : 1). Diarylalkyne 2a (0.57 g, 70%) was isolated as yellow crystals, m.p. 245-249 C. HRMS (ESI), found m/z: 325.1179, 347.0997; C18H16N2O4; calculated 325.1183 [M + H]+, 347.1002 [M + Na]+. IR (KBr), nu/cm-1:788, 834, 985, 1103, 1162, 1235, 1300, 1430, 1506-1663, 1688, 2342, 2361, 2838-3033, 3367, 3464. 1H NMR (DMSO-d6), delta: 3.82 (s, 6 H, 2 MeO); 6.75 (d, 2 H, HC(5), HC(5), J = 8.6 Hz); 7.26 (dd, 2 H, HC(4), HC(4), J = 8.6 Hz, J = 1.9 Hz); 7.83 (d, 2 H, HC(2), HC(2), J = 1.9 Hz). 13C NMR (DMSO-d6), delta: 51.3 (Me, Me); 86.9 (CC); 108,8 (C(5), C(5)); 109.0 (C(3), C(3)); 116.9 (C(1), C(1)); 133.9 (C(2), C(2)); 136.0 (C(4), C(4)); 150.8 (C(6), C(6)); 167.1 (CO, CO).

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

Reference:
Article; Lozanova; Stepanov; Mel?nik; Zlokazov; Veselovsky; Russian Chemical Bulletin; vol. 68; 1; (2019); p. 64 – 67; Izv. Akad. Nauk, Ser. Khim.; 1; (2019); p. 64 – 67,4;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 77317-55-6, 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. 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

b) (2-Amino-5-iodo-phenyl)-methanol; Intermediate 17a (14.00 g) was dissolved in dry THF (50 ml_) and 1M diisobutylaluminium hydride in THF (165 ml_) was added dropwise to this solution at -30C. The solution was then stirred at -150C for 1 h. To this mixture MeOH (50 mL) was added portionwise maintaining the temperature of the solution below -5C. The resulting mixture was then at -15C for 18 h. The formed solid was filtered off and washed with MeOH. The organic phase was dried and the solvent was evaporated in vacuo. The residue was purified by flash chromatography (silica gel, 1-5% methanol in dichloromethane) to give the title compound (9.70 g); ESMS m/z 249.9 [M+H]+.

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

Related Products of 77317-55-6, A common heterocyclic compound, 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, molecular formula is C8H8INO2, 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.

REFERENCE EXAMPLE 108 2-Amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)benzoic acid methyl ester To a solution of methyl 5-iodoanthranilate (2.87 g, 10.0 mmol) and triethylamine (4.2 mL, 30 mmol) in 1,4-dioxane (20 mL), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (82 mg, 0.10 mmol) was added and 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3.7 mL, 25 mmol) was added dropwise. The resultant mixture was stirred at 80 C for 14 hours under nitrogen atmosphere. The reaction mixture was combined with water, and extracted twice with ethyl acetate. The combined organic layer was washed with water and brine, filtered through a silica gel (eluding with ethyl acetate), and concentrated under reduced pressure. The residue was subjected to a column chromatography on a silica gel (hexane/ethyl acetate, 5:1), and recrystallized from ethyl acetate-hexane to obtain the title compound (1.45 g, yield: 52%). Melting point: 110-112 C 1H NMR (CDCl3) delta 1.33 (12H, s), 3.86 (3H, s), 5.96 (2H, br s), 6.63 (1H, d, J = 8.3 Hz), 7.67 (1H, dd, J = 8.3, 1.5 Hz), 8.33 (1H, d, J = 1.5 Hz).

The synthetic route of 77317-55-6 has been constantly updated, and we look forward to future research findings.