Ethyl Acrylate → 3-(4-Benzyloxycarbonylamino-2-fluoro-phenyl)-acrylic Acid Ethyl Ester

HRID 2193544Notes

Reaction equation

[CH2:1]([O:8][C:9](=[O:19])[NH:10][C:11]1[CH:16]=[CH:15][C:14](Br)=[C:13]([F:18])[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]([O:24][CH2:25][CH3:26])(=[O:23])[CH:21]=[CH2:22].CCN(C(C)C)C(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:25]([O:24][C:20](=[O:23])[CH:21]=[CH:22][C:14]1[CH:15]=[CH:16][C:11]([NH:10][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:19])=[CH:12][C:13]=1[F:18])[CH3:26]

Participants

Conditions

Temperature: 130 °C

Procedure

A suspension of 9.72 g (4-bromo-3-fluoro-phenyl)-carbamic acid benzyl ester (30 mmol), 6 g ethyl acrylate (60 mmol), 10.2 ml DIPEA (60 mmol), 112 mg palladium acetate (, 3 mmol), and 1.57 g triphenylphosphine (6 mmol) in 10 ml DMF were stirred at 130° C. for 48 h. The reaction was monitored by TLC. The DMF was evaporated, the residue dissolved in dichloromethane, washed with water and brine, dried over Mg sulfate, filtered and the filtrate evaporated. The residue was purified by chromatography, using a 7/3 N-hexane/ethyl acetate mixture as eluent.

Workup

customThe DMF was evaporated
dissolutionthe residue dissolved in dichloromethane
washwashed with water and brine
dry with materialdried over Mg sulfate
filtrationfiltered
customthe filtrate evaporated
customThe residue was purified by chromatography

Sources & evidence

ORD record: ord-7a08d077fcd8453c83d889a111c44fb8
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329908B2

Reaction notes

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