Ethyl 5-Bromoindole-2-carboxylate → 2-(1H-Indol-2-yl)acetamide

HRID 1677803노트

반응식

HRID 1677803 반응식
C(O[C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11](Br)=[CH:10][CH:9]=2)=O)C.[NH3:16].[CH3:17][OH:18]>>[NH:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:14]=[C:6]1[CH2:4][C:17]([NH2:16])=[O:18]

참가 물질

3

반응물 2

HCID 259091Ethyl 5-Bromoindole-2-carboxylateHCID 21705897Ammonia methanol

생성물 1

HCID 186542632-(1H-Indol-2-yl)acetamide

실험 절차

Treat 5-bromo-1H-indole-2-carboxylic acid ethyl ester 1 (X═Br, 4.67 mmol) with 7 N NH3/MeOH as described in General Synthetic Procedure III to afford 5-bromo-1H-indole-2-carboxylic acid amide 4 (X═Br, R2═R3═H) as an ivory-colored solid. Treat 5-bromo-1H-indole-2-carboxylic acid amide (100 mg, 0.41 mmol) with diphenyldisulfide (1.50 equiv., 141 mg, 0.65 mmol) as described in General Synthetic Procedure VIIb to give the title compound Id (85 mg) as an ivory-colored solid. 1H NMR (DMSO-d6) δ 12.5 (brs, 1H), 8.0 (brs, 1H), 7.72 (brs, 1H), 7.59-7.08 (m, 8H); LC/MS: m/z obs=347 (M+1).

출처 및 근거

ORD 기록
ord-56fb2f6534f641ceb5370e648a45d6e1
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08008340B2

반응 노트

불러오는 중…