Benzo(B)Thiophene-2-Boronic Acid → (6-Benzo[b]thiophen-2-yl-2-methoxy-pyrimidin-4-yl)-[2-(4-methoxy-phenyl)-ethyl]-amine

Participants

Reaction Steps

By proceeding in a similar manner as above in Example 10(a) but using (6-chloro-2-methoxy-pyrimidin-4-yl)-[2-(4-methoxy-phenyl)-ethyl]-amine (150 mg), benzo[b]thiophene-2-boronic acid (182 mg), Cs2CO3 (590 mg) and tetrakis(triphenylphosphine)palladium (0) (58 mg), and subjecting the crude reaction product to flash column chromatography on silica gel eluting with a mixtures of 20 to 100% EtOAc and cyclohexane, there is prepared (6-benzo[b]thiophen-2-yl-2-methoxy-pyrimidin-4-yl)-[2-(4-methoxy-phenyl)-ethyl]-amine [85 mg, 42% yield, Example 10(g)]. LCMS: RT=10.39 minutes, MS: 392 (M+H). IC50=5.1 nM

Provenance & Evidence