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

HRID 1163341Notes

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-c1d27a6614b24fdda28a9b9d81e4992a
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820823B2

Reaction notes

Loading…