Acetyl chloride → methyl 3-acetyl-1-butyl-1H-indole-6-carboxylate

HRID 349012

Reaction equation

[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=2)[CH:7]=[CH:6]1)[CH2:2][CH2:3][CH3:4].[Cl-].C([Al+]CC)C.[C:24](Cl)(=[O:26])[CH3:25]>ClCCl>[C:24]([C:7]1[C:8]2[C:13](=[CH:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:9]=2)[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH:6]=1)(=[O:26])[CH3:25]

Participants

Conditions

Temperature: 0 °C

Procedure

Methyl 1-butyl-1H-indole-6-carboxylate (4.53 g) was dissolved in dichloromethane (25 ml). The mixture was cooled to 0° C. Diethyl aluminum chloride was added dropwise (29.5 mL) and the mixture was allowed to stir at 0° C. for 30 min. A solution of dichloromethane (25 mL) and acetyl chloride (2.1 mL) was added dropwise, and the mixture was stirred for 2 h at 0° C. The mixture was then partitioned between dichloromethane, water, and brine, dried over sodium sulfate, filtered, and concentrated. The concentrate was chromatographed on silica gel using ethyl acetate/heptane (40/60) to give methyl 3-acetyl-1-butyl-1H-indole-6-carboxylate (3.38 g). MS (ESI+) for C16H19N1O3+H1 m/z 274.14 (M+H)+.

Workup

stirringthe mixture was stirred for 2 h at 0° C
customThe mixture was then partitioned between dichloromethane, water, and brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe concentrate was chromatographed on silica gel

Sources & evidence

ORD record: ord-b96b2dd042e04d8088497e16dbbf655d
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07176242B2

Linked notes

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