Methanol → 4-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2-yl]-2-chloro-benzoic acid methyl ester

HRID 241521Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][C:10]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=3)([C:13]([F:16])([F:15])[F:14])[CH2:11][N:12]=2)=[CH:4][C:3]=1[Cl:25].[C:26]([O-:29])(=[O:28])C.[Na+].[CH3:31]O>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:31][O:29][C:26](=[O:28])[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][C:10]([C:17]3[CH:18]=[C:19]([Cl:24])[CH:20]=[C:21]([Cl:23])[CH:22]=3)([C:13]([F:16])([F:14])[F:15])[CH2:11][N:12]=2)=[CH:4][C:3]=1[Cl:25]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 5-(4-bromo-3-chloro-phenyl)-3-(3,5-dichloro-phenyl)-3-trifluoromethyl-3,4-dihydro-2H-pyrrole (10.60 g), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) (1.645 mg), sodium acetate (2.748 g) and methanol (100 mL) was placed in an autoclave and purged with CO gas. The pressure was adjusted to 5 bar and the mixture was heated at 80° C. for 16 h. After cooling the pressure was released and the solvents were distilled off in vacuum. The residue was purified by flash chromatography on silica gel to give the title compound (10.00 g, 99%).

Workup

custompurged with CO gas
temperatureAfter cooling the pressure
distillationthe solvents were distilled off in vacuum
customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-ab9073be8b0342ada2cc56e59ecdc24e
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653000B2

Reaction notes

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