Dimethylformamide → HCID 74018211, compound

HRID 1819509Notes

Reaction equation

[CH3:1][N:2]([CH:4]=[O:5])C.[F:6][C:7]1[C:12]([CH:13]([O:19][CH3:20])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:11][CH:10]=[CH:9][C:8]=1[C:21]1[N:22]=C(N)[S:24][CH:25]=1.[CH2:27]([O:29][C:30](=[O:43])[C:31]([CH3:42])=[CH:32][C:33]1[C:38]([F:39])=[CH:37][C:36](Br)=[CH:35][C:34]=1[F:41])[CH3:28].C(N(CC)CC)C>O>[F:39][C:38]1[CH:37]=[C:36]([C:4](=[O:5])[NH:2][C:1]2[S:24][CH:25]=[C:21]([C:8]3[CH:9]=[CH:10][CH:11]=[C:12]([CH:13]([O:19][CH3:20])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:7]=3[F:6])[N:22]=2)[CH:35]=[C:34]([F:41])[C:33]=1[CH:32]=[C:31]([CH3:42])[C:30]([O:29][CH2:27][CH3:28])=[O:43]

Participants

Conditions

Temperature: 85 °C

Procedure

To a DMF (6 mL) solution of 4-[2-fluoro-3-(1-methyloxyhexyl)phenyl]thiazol-2-ylamine (318 mg), 3-(4-bromo-2,6-difluoropheny)-2-methylacrylic acid ethyl ester (300 mg), and dichlorobistriphenylphosphinepalladium (36 mg) was added triethylamine (0.43 mL). The reaction mixture was stirred under carbon monoxide atomosphere at 85° C. for 16 h. Water was poured into the reaction mixture, and the reaction mixture extracted with ethyl acetate, and the organic layer was washed with water, and brine, dried over magnesium sulfate, and evaporated. The obtained residue was purified by Colum chromatography (hexane:ethyl acetate=4:1) to obtain the compound (20) 500 mg.

Workup

extractionthe reaction mixture extracted with ethyl acetate
washthe organic layer was washed with water, and brine
dry with materialdried over magnesium sulfate
customevaporated
customThe obtained residue was purified by Colum chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record: ord-bce18521165041b7a5526042a6f8c3c4
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601746B2

Reaction notes

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