Water → N1-cyclopropyl-5-((2-amino-4-pyridyl)oxy)-1H-1-indolecarboxamide

HRID 387827Notes

Reaction equation

[H-].[Na+].[NH2:3][C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:15]=[CH:14]3)[CH:7]=[CH:6][N:5]=1.[CH:20]1([NH:23][C:24](=O)[O:25]C2C=CC=CC=2)[CH2:22][CH2:21]1.O>CN(C)C=O>[CH:20]1([NH:23][C:24]([N:16]2[C:17]3[C:13](=[CH:12][C:11]([O:10][C:8]4[CH:7]=[CH:6][N:5]=[C:4]([NH2:3])[CH:9]=4)=[CH:19][CH:18]=3)[CH:14]=[CH:15]2)=[O:25])[CH2:22][CH2:21]1

Participants

Conditions

Temperature: 0 °C

Procedure

After adding 28 mg of sodium hydride (60% in oil) to a solution of 150 mg of 5-[(2-amino-4-pyridyl)oxy]-1H-indole in dimethylformamide at room temperature and stirring for 5 minutes, the mixture was cooled to 0° C., 124 mg of phenyl N-cyclopropylcarbamate was added and the mixture was further stirred for 30 minutes. Water was added, extraction was performed with ethyl acetate, the organic layer was washed 3 times with water and once with ammonium chloride water, and then silica gel was added and the solvent was distilled off under reduced pressure. The silica gel was charged into a dry column packed with silica gel and purification was performed by column chromatography (hexane:ethyl acetate=1:1, followed by ethyl acetate), to obtain 2.4 g of a colorless powder.

Workup

stirringthe mixture was further stirred for 30 minutes
extractionextraction
washthe organic layer was washed 3 times with water
additiononce with ammonium chloride water, and then silica gel was added
distillationthe solvent was distilled off under reduced pressure
additionThe silica gel was charged into a dry column
custompacked with silica gel and purification

Sources & evidence

ORD record: ord-64f1e599f0124527aebf5fd2afb0f077
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372981B2

Reaction notes

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