Dimethylformamide → HCID 117778812, compound

HRID 2206509Notes

Reaction equation

[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1C(OC)=O)=[CH:8][CH:7]=[CH:6][CH:5]=2.[C:15](=[O:18])([O-])[O-:16].[Cs+].[Cs+].Br[CH:22]([CH2:24][CH3:25])[CH3:23].[CH3:26]N(C)C=O>>[CH:22]([N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:10][C:2]1([CH3:1])[C:15]([O:16][CH3:26])=[O:18])([CH2:24][CH3:25])[CH3:23]

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 65542-Bromobutane

HCID 10796Cesium carbonate

HCID 594174Methyl 2-methyl-1H-indole-3-carboxylate

Product 1

HCID 117778812HCID 117778812, compoundYield 22%

Conditions

Temperature: 100 °C

Procedure

To a solution of methyl 2-methyl-1H-indole-3-carboxylate (0.5 g, 2.6 mmol) in N,N-dimethylformamide (20 mL) was added cesium carbonate (1.7 g, 5.2 mmol) and 2-bromobutane (0.71 g, 5.2 mmol), the mixture was stirred at 100° C. under microwave for 1 hour, the mixture was concentrated and purified by column chromatography (silica gel, ethyl acetate/petroleum ether=1:20) to give methyl 1-sec-butyl-2-methyl-1H-indole-carboxylate (141 mg, 22%).

Workup

concentrationthe mixture was concentrated
custompurified by column chromatography (silica gel, ethyl acetate/petroleum ether=1:20)

Sources & evidence

ORD record: ord-e4a9f2e0ad654fb0a6d6fca1ad414611
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371331B2

Reaction notes

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