3-(6-Bromo-2-methyl-1H-indol-3-ylsulfanyl)-benzoic acid methyl ester → 3-(6-Cyano-2-methyl-1H-indol-3-ylsulfanyl)-benzoic acid methyl ester

HRID 1466930

반응식

HRID 1466930 반응식
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][C:11]2[C:19]3[C:14](=[CH:15][C:16](Br)=[CH:17][CH:18]=3)[NH:13][C:12]=2[CH3:21])[CH:5]=1.[Cu][C:24]#[N:25]>CS(C)=O>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][C:11]2[C:19]3[C:14](=[CH:15][C:16]([C:24]#[N:25])=[CH:17][CH:18]=3)[NH:13][C:12]=2[CH3:21])[CH:5]=1

참가 물질

4

반응물 2

HCID 667653623-(6-Bromo-2-methyl-1H-indol-3-ylsulfanyl)-benzoic acid methyl esterHCID 178418546HCID 178418546, 화합물

생성물 1

HCID 667650153-(6-Cyano-2-methyl-1H-indol-3-ylsulfanyl)-benzoic acid methyl ester

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
130 °C

실험 절차

3-(6-Bromo-2-methyl-1H-indol-3-ylsulfanyl)-benzoic acid methyl ester (0.19 g, 0.5 mmol) and copper(I) cyanide (0.090 g, 1.0 mmol) were combined in DMSO (10 mL) in a sealed reaction vessel and stirred at 130° C. for overnight. The resulting mixture was cooled to room temperature, and subjected to standard aqueous workup. The crude residue was purified by silica gel chromatography (10-100% EtOAc in hexanes) to afford the title compound.

후처리

  1. temperatureThe resulting mixture was cooled to room temperature
  2. customThe crude residue was purified by silica gel chromatography (10-100% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-db0ee61546dd4ff39c5e898034005119
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000025B2

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