Sodium Carbonate → HCID 57937834, compound

Participants

Reaction Conditions

Reaction Steps

(4-Bromo-3-methyl-benzyl)-(3-methyl-butyl)-carbamic acid tert-butyl ester (I-2c: 250 mg, 0.675 mmol) was added to a 5 mL microwave vial and dissolved in 2 mL of 1,2-dimethoxyethane. To this solution was added 4-nitro-phenyl boronic acid (146 mg, 0.878 mmol) and 1 mL of a 2M aqueous sodium carbonate solution and tetrakis(triphenylphosphine) palladium (0.040 g, 0.0338 mmol). The reaction mixture was purged with nitrogen and sealed before heating to 80° C. by microwave irradiation for 15 minutes. The reaction mixture was diluted with water (10 mL) and extracted with ethyl acetate (2×10 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified using preparative thin layer chromatography eluting with 15% ethyl acetate in heptane. Collection and extraction of the product-containing band followed by concentration under reduced pressure afforded the title compound (I-8a: 0.150 g).

Provenance & Evidence