Sodium Carbonate → 2-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzaldehyde

HRID 1433203Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 5-bromo-2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazole (0.700 g, 1.89 mmol), 2-formylphenylboronic acid (0.424 g, 2.83 mmol), sodium carbonate (1.200 g, 11.3 mmol), and 1,1′-[bis(di-tert-butylphosphino)ferrocene]-palladium dichloride (0.123 g, 0.189 mmol) in DME (14 mL) and H2O (3.5 mL) was heated at 90° C. for 12 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by chromatography (silica, hexanes: EtOAc, 1:1) to afford the product as a yellow oil (0.568 g, 76%).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe residue was purified by chromatography (silica, hexanes: EtOAc, 1:1)

Sources & evidence

ORD record: ord-0e0b10048031419ebd2e87ef0001963d
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612211B2

Reaction notes

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