Dimethylamine tetrahydrofuran → 4-(Benzyloxy)-N,N,2-trimethyl-1-tosyl-1H-benzo[d]imidazole-6-carboxamide

Temperatur

65 °C

A mixture of 6-bromo-2-methyl-1-[(4-methylphenyl)sulfonyl]-4-[(phenylmethyl)oxy]-1H-benzimidazole (53.0 g, 112 mmol, STEP 2) and tetrakis(triphenylphosphine)palladium(0) (25.9 g, 22.4 mmol) in 2M dimethylamine tetrahydrofuran solution (580 mL) was stirred at 65° C. under carbon mono-oxide gas (1 atmosphere) for 32 hours. The mixture was cooled to room temperature, and diluted with ethyl acetate (600 mL). The organic mixture was washed with saturated ammonium chloride aqueous solution (800 mL) and brine (500 mL), dried over magnesium sulfate and concentrated in vacuum. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate gradient elution from 1:2 to 1:3) to afford the title compound as a white solid (21.8 g, 42%).

1. temperatureThe mixture was cooled to room temperature
2. washThe organic mixture was washed with saturated ammonium chloride aqueous solution (800 mL) and brine (500 mL)
3. dry with materialdried over magnesium sulfate
4. concentrationconcentrated in vacuum
5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate gradient elution from 1:2 to 1:3)

ORD-Eintrag

ord-6d5cb90a823b4ba69bc72c8abc6d4df6

Quelldatensatz

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07723321B2