Methyl Acrylate → HCID 22467387, compound

HRID 1934706Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([F:22])=[C:6]([CH:21]=1)[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)=[O:8].[C:23]([O:27][CH3:28])(=[O:26])[CH:24]=[CH2:25].C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:20][O:19][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][C:14]=1[O:17][CH3:18])[CH2:10][NH:9][C:7](=[O:8])[C:6]1[CH:21]=[C:2](/[CH:25]=[CH:24]/[C:23]([O:27][CH3:28])=[O:26])[CH:3]=[CH:4][C:5]=1[F:22]

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 5-bromo-N-(3,4-dimethoxybenzyl)-2-fluorobenzamide (200 mg) in dimethylformamide (2 mL) were added methyl acrylate (0.068 mL), triethylamine (0.09 mL) and dichlorobis(triphenylphosphine)pailadium(II) (13.4 mg), and the mixture was stirred for 6 hours at 120° C. in a sealed tube. The resulting mixture was diluted with ethyl acetate and washed successively with water and brine. The organic layer was dried over sodium sulfate and evaporated in vacuo. The residue was subjected to a silica gel column chromatography eluting with a mixture of chloroform and ethyl acetate (9:1) to give N-(3,4-dimethoxybenzyl)-2-fluoro-5-[trans-2-(methoxycarbonyl)ethenyl]benzamide (117 mg) as a solid substance.

Workup

washwashed successively with water and brine
dry with materialThe organic layer was dried over sodium sulfate
customevaporated in vacuo
washeluting with a mixture of chloroform and ethyl acetate (9:1)

Sources & evidence

ORD record: ord-9605e40ab557485e8dd6874b06029fed
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06384080B1

Reaction notes

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