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

反応式

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]

参加物

反応物 2

HCID 259091Ethyl 5-Bromoindole-2-carboxylate

HCID 21705897Ammonia methanol

生成物 1

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

実験手順

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).

出典と根拠

ORDレコード: ord-56fb2f6534f641ceb5370e648a45d6e1
出典データセット: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08008340B2

反応ノート

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