Methyl Acrylate → HCID 58600634, compound

HRID 488875Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[O:8][C:7](=[O:13])[C:6]([CH2:14][C:15]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[C:25]([F:28])([F:27])[F:26])=[O:16])=[C:5]2[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[C:35]([O:39][CH3:40])(=[O:38])[CH:36]=[CH2:37].CCN(CC)CC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2].O>[F:24][C:21]1[CH:22]=[CH:23][C:18]([NH:17][C:15](=[O:16])[CH2:14][C:6]2[C:7](=[O:13])[O:8][C:9]3[C:4]([C:5]=2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:3][C:2](/[CH:37]=[CH:36]/[C:35]([O:39][CH3:40])=[O:38])=[C:11]([CH3:12])[CH:10]=3)=[C:19]([C:25]([F:28])([F:26])[F:27])[CH:20]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A solution of 2-(6-bromo-7-methyl-2-oxo-4-phenyl-2H-chromen-3-yl)-N-[4-fluoro-2-(trifluoromethyl)phenyl]acetamide (Example 177) (500 mg) in DMF (5 mL) was combined with methyl acrylate (0.14 mL), Et3N (0.21 mL), Pd(OAc)2 (5 mg) and triphenylphosphine (10 mg) under argon atmosphere, and stirred with heating at 120° C. for 10 hours. The reaction solution was combined with water and extracted with ethyl acetate. The extract was washed with diluted hydrochloric acid followed by an aqueous solution of NaHCO3 and water, and then dried over magnesium sulfate, and concentrated under reduced pressure to obtain the title compound as a colorless crystal (360 mg, yield: 72%). An aliquot was recrystallized from ethyl acetate to measure a melting point. Melting point: 233-236° C.

Workup

extractionextracted with ethyl acetate
washThe extract was washed with diluted hydrochloric acid
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-e8add3ef3415471db261a23ac356502c
Source dataset: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06974806B2

Reaction notes

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