Sodium Carbonate → 1-{2-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-phenyl}-ethanone

HRID 1433213Notes

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.[C:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1B(O)O)(=[O:25])[CH3:24].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:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=4[C:23](=[O:25])[CH3:24])=[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 (0.450 g, 1.21 mmol), 2-acetylphenylboronic acid (0.298 g, 1.82 mmol), sodium carbonate (0.771 g, 7.26 mmol), and 1,1′-[bis(di-tert-butylphosphino)ferrocene]-palladium dichloride (0.079 g, 0.121 mmol) in DME (10 mL) and H2O (2.5 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 (0.433 g, 87%).

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-5caf0498e5574e7c8a0fdeabab897ab0
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612211B2

Reaction notes

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