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

HRID 241526Notes

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:26]([O-])([O-])=[O:27].[Na+].[Na+].C([SiH](CC)CC)C>CN(C)C=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]>[Cl:24][C:19]1[CH:18]=[C:17]([C:10]2([C:13]([F:16])([F:15])[F:14])[CH2:9][C:8]([C:5]3[CH:6]=[CH:7][C:2]([CH:26]=[O:27])=[C:3]([CH3:25])[CH:4]=3)=[N:12][CH2:11]2)[CH:22]=[C:21]([Cl:23])[CH:20]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of 5-(4-bromo-3-methyl-phenyl)-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-2,4-dihydropyrrole (i.e. the product of Step 4, 2.0 g) in dimethylformamide (DMF) (50 mL) was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (“Pd(dppf)Cl2”, 0.16 g), Na2CO3 (0.59 g) and triethylsilane (1.4 mL). The mixture was purged twice with N2, then purged three times with CO and stirred under an atmosphere of CO overnight at 65° C. Then, the reaction was concentrated in vacuum and purified by flash chromatography on silica gel to afford the title compound (1.32 g, 74%).

Workup

customThe mixture was purged twice with N2
custompurged three times with CO
concentrationThen, the reaction was concentrated in vacuum
custompurified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-de48fac1d2d04dec84902e698edeb682
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653000B2

Reaction notes

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