Ethyl 5-Bromoindole-2-carboxylate → 1H-Indoleacetamide

HRID 1677803Notes

Reaction equation

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]

Participants

Reactant 2

HCID 259091Ethyl 5-Bromoindole-2-carboxylate

HCID 21705897Ammonia methanol

Product 1

HCID 186542631H-Indoleacetamide

Procedure

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).

Sources & evidence

ORD record: ord-56fb2f6534f641ceb5370e648a45d6e1
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008340B2

Reaction notes

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