Sodium Carbonate → 7-(3-Aminophenyl)-1-phenyl-5-trifluoromethylbenzimidazole

A mixture of 7-iodo-1-phenyl-5-trifluoromethylbenzimidazole (3.2 g, 8.2 mmol), 3-aminophenyl boronic acid (1.68 g, 12.3 mmol), sodium carbonate (5.68 g, 41 mmol), 1,3-propanediol (2.94 ml, 41 mmol) and bis(triphenylphosphin)palladium dichloride (200 mg, 0.28 mmol) in a mixture of water (13 ml) and dimethoxyethane (26 ml) was stirred at reflux overnight The cooled reaction mixture was partitioned between ethyl acetate and water, and the organic extract was purified by column chromatography on silica gel eluting with a mixture of dichloromethane and methanol (99:1, v/v). The product was isolated by removal of solvent from appropriate eluate fractions followed by crystallisation of the residue from 2-propanol (50 ml). Yield: 2.7 g (93%), m/z, 354.1 (M+H)+.

1. temperatureat reflux overnight
2. customThe cooled reaction mixture
3. customwas partitioned between ethyl acetate and water
4. extractionthe organic extract
5. customwas purified by column chromatography on silica gel eluting with a mixture of dichloromethane and methanol (99:1
6. customThe product was isolated by removal of solvent from appropriate eluate fractions
7. customfollowed by crystallisation of the residue from 2-propanol (50 ml)

ORD record

ord-8716852b8a594a40a2d729d2e5d52845

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07700638B2