Diisopropylamine → HCID 66690551, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3-bromo-4-hydroxy-5-nitrobenzoate (1.0 g, 3.62 mmol), (4-fluorophenyl)-boronic acid (0.76 g, 5.43 mmol), 3,3′,3″-phosphinidynetris (benzensulfonic acid) trisodium salt (0.17 mg, 0.27 mmol), palladium(II) acetate (20.0 mg, 0.09 mmol) and diisopropylamine (0.52 mL, 3.62 mmol) were added N,N-dimethylformamide (13.6 mL) and water (4.5 mL). The mixture was heated to 80° C. After 18 h, the mixture was cooled to ambient temperature and ethyl acetate was added. The organic layer was washed with water (3×), brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% hexanes→25% hexanes/ethyl acetate). Another purification using reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (0.43 g). LC-MS [M+1]=291.9.

Provenance & Evidence