Ethyl Acetate → HCID 57890344, compound

HRID 1820011Notes

Reaction equation

Br[C:2]1[CH:25]=[CH:24][C:5]([C:6]([NH:8][CH2:9][CH:10]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=[CH:14][CH:13]=2)[CH3:11])=[O:7])=[C:4]([F:26])[CH:3]=1.[Cl:27][C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>O1CCCC1>[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([C:2]2[CH:25]=[CH:24][C:5]([C:6]([NH:8][CH2:9][CH:10]([C:12]3[CH:17]=[CH:16][C:15]([CH2:18][N:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)=[CH:14][CH:13]=3)[CH3:11])=[O:7])=[C:4]([F:26])[CH:3]=2)=[CH:30][CH:29]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution (7 ml) of 4-bromo-2-fluoro-N-{2-[4-(1-pyrrolidinylmethyl)phenyl]propyl}benzamide (300 mg, 0.715 mmol) obtained in Example 5, 4-chlorophenylboronic acid (224 mg, 1.43 mmol) and 2N aqueous sodium carbonate solution (0.715 ml) in tetrahydrofuran was added tetrakistriphenylphosphine palladium (24.8 mg, 21.5 mmol) under a nitrogen atmosphere. This was stirred at 90° C. for 16 hrs, and allowed to cool to room temperature. Ethyl acetate was added to the reaction mixture, and the mixture was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by NH-silica gel column chromatography (developing solvent; ethyl acetate), and powderized with isopropyl ether to give the title compound (142 mg).

Workup

temperatureto cool to room temperature
washthe mixture was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customthe obtained residue was purified by NH-silica gel column chromatography (developing solvent; ethyl acetate)

Sources & evidence

ORD record: ord-bec5ce6c9c2c47e3abf96f70523d5b93
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601868B2

Reaction notes

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