Sodium Carbonate → 4-[3-(3,5-Dichlorophenyl)-3-(trifluoromethyl)-2,4-dihydropyrrol-5-yl]-2-methyl-benzaldehyde

HRID 241514Notes

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[CH3:25].C([SiH](CC)CC)C.[C:33]([O-])([O-])=[O:34].[Na+].[Na+]>CN(C=O)C.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]>[Cl:24][C:19]1[CH:18]=[C:17]([C:10]2([C:13]([F:16])([F:15])[F:14])[CH2:11][N:12]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([CH:33]=[O:34])=[C:3]([CH3:25])[CH:4]=3)[CH2:9]2)[CH:22]=[C:21]([Cl:23])[CH:20]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 5-(4-bromo-3-methyl-phenyl)-3-(3,5-dichloro-phenyl)-3-trifluoromethyl-3,4-dihydro-2H-pyrrole (2.00 g, 4.43 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) (162 mg, 0.229 mmol), triethylsilane (1.42 mL, 1.03 g, 8.87 mmol) and Na2CO3 (587 mg, 5.54 mmol) in DMF (30 mL) were purged with CO gas at 65° C. The mixture was stirred over night at 65° C. and then cooled to room temperature. The residue was purified by flash chromatography on silica gel to give the title compound (1.316 g, 74%).

Workup

customwere purged with CO gas at 65° C
temperaturecooled to room temperature
customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-a3d93920985447f2833522beb61407f7
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653000B2

Reaction notes

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