Cesium carbonate → 6-(4-fluorophenyl)-7-methoxy-4-[[4-(piperidin-1-ylmethyl)anilino]methylidene]isoquinoline-1,3-dione

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-Bromo-7-methoxy-4-[(4-piperidin-1-ylmethyl-phenylamino)-methylene]-4H-isoquinoline-1,3-dione (272 mg, 0.578 mmole), N,N-dimethylformamide (2 mL), 4-fluorophenylboronic acid (202 mg, 1.44 mmole), tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct (78 mg, 0.075 mmole), tri(t-butyl)phosphine (28 mg, 0.138 mmole) and cesium carbonate (377 mg, 1.16 mmole) is stirred and heated at 110° C. for one hour, cooled in the refrigerator. The reaction mixture is evaporated to dryness, taken up in 5% methanol in chlororform and passed through a short pad of Florisil eluting with 5% methanol in chloroform. The eluate is evaporated in vacuo and treated with acetonitrile, filtered and dried to give a yellow-brown solid 138 mg (48%), mp 227-230° C.; MS (ESI): m/z 486.2 (M+H).

Provenance & Evidence