Dimethylformamide → 1-(2-acetyloxyethyl)-N-(3-cyano-4-neopentyloxyphenyl)-5-fluoro-2-methylindole-3-carboxamide

HRID 2216411Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([NH:15][C:16]([C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([F:27])[CH:25]=3)[NH:20][C:19]=2[CH3:28])=[O:17])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])#[N:2].C(=O)([O-])[O-].[K+].[K+].[C:35]([O:38][CH2:39][CH2:40]Br)(=[O:37])[CH3:36].CN(C)C=O>O>[C:35]([O:38][CH2:39][CH2:40][N:20]1[C:21]2[C:26](=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[C:18]([C:16]([NH:15][C:5]2[CH:6]=[CH:7][C:8]([O:9][CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[C:3]([C:1]#[N:2])[CH:4]=2)=[O:17])=[C:19]1[CH3:28])(=[O:37])[CH3:36]

Participants

Conditions

Temperature: 40 °C

Procedure

N-(3-Cyano-4-neopentyloxyphenyl)-5-fluoro-2-methyl-1H-indole-3-carboxamide ¼ hydrate (0.8 g) obtained in Example 9,. potassium carbonate (0.2 g) and 2-bromoethyl acetate (0.4 g) were added to dimethylformamide (5 ml) and the mixture was stirred at 40° C. for 3 hr. Then the reaction mixture was treated with water and the oganic layer was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and the solvent was evaporated. The residue was separated and purified by silica gel column chromatography (mobile phase: chloroform) to give the title compound (0.3 g). melting point: 124-125° C.

Workup

extractionthe oganic layer was extracted with ethyl acetate
dry with materialThe extract was dried over anhydrous magnesium sulfate
customthe solvent was evaporated
customThe residue was separated
custompurified by silica gel column chromatography (mobile phase: chloroform)

Sources & evidence

ORD record: ord-000fcc7f54a2482fac3279dd1833830d
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07112594B2

Reaction notes

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