5-chloro-2-methoxy-4-(2-oxoethyl)benzonitrile

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 5-(2-piperazin-1-ylethyl)-2-benzofuran-1(3H)-one (90 mg, 0.190 mmol) and NaBH3CN (24 mg, 0.380 mmol) in 20 mL DCM was added 5-chloro-2-methoxy-4-(2-oxoethyl)benzonitrile (40 mg, 0.190 mmol) and the mixture was stirred at RT overnight. Concentrated, and the residue was purified by prep-TLC to give 5-chloro-2-methoxy-4-(2-{4-[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl)benzonitrile. 1H-NMR (400 MHz, MeOD) δ ppm 7.82 (d, J=7.8 Hz, 1H), 7.67 (s, 1H), 7.50˜7.53 (m, 2H), 7.20 (s, 1H), 5.35 (s, 2H), 3.95 (s, 3H), 3.23˜3.26 (m, 6H), 3.10˜3.16 (m, 8H), 3.00˜3.03 (m, 2H). MS m/e 441 (M+1)+. (0.094 μM) Concentrated the residue was purified by prep-TLC