Potassium Carbonate → Isohexane ethyl acetate

Participants

Reaction Conditions

Reaction Steps

A solution of tert-butyl 4-[(6-bromo-1-oxo-1,2-dihydroisoquinolin-4-yl)sulfonyl]piperazine-1-carboxylate (Example 47a, 1.70 g) in 1-methyl-2-pyrrolidinone (10 mL) was treated with (bromomethyl)cyclopropane (0.41 mL) and potassium carbonate (0.796 g). The resulting mixture was stirred at 70° C. overnight. The cooled reaction mixture was partitioned between water (250 mL) and ethyl acetate. The organic was separated and the aqueous extracted with further ethyl acetate. The combined organics were washed with water (2×200 mL) and brine (100 mL), dried (MgSO4), filtered and concentrated to dryness. The residue was purified (SiO2 chromatography, elution 10% ethyl acetate/isohexane then 50% ethyl acetate/isohexane) to afford the subtitle compound (0.890 g) as a pale yellow solid.

Provenance & Evidence