4-(1-Piperidylmethyl)phenylboronic Acid → HCID 58266539, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 9-benzenesulfonyl-3-bromo-5-hydroxy-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (150 mg, 0.35 mmol), 4-piperidin-1-ylmethylphenyl boronic acid (126 mg, 0.6 mmol) and [1,1′-bis(diphenylphosphino) ferrocene]dichloropalladium(II) (27 mg, 0.04 mmol) in 2N aqueous potassium acetate (1.1 mL) and acetonitrile (1.4 mL) was heated under microwave irradiation at 140° C., for 30 minutes. The reaction mixture was diluted with ethyl acetate (10 mL) and water (10 mL) resulting in the formation of a precipitate. The supernatant liquors were decanted and the precipitate was dissolved in 10% methanol in DCM. The decanted liquors were partitioned and the aqueous phase was washed with 10% methanol in DCM (2×10 mL). The combined organic phases were concentrated in vacuo and the resultant residue purified by column chromatography (silica, 2 g cartridge, Si-SPE, 0-20% MeOH in DCM) afforded the crude product which was triturated with acetonitrile (1 mL) and methanol (1 mL) to afford the title compound as a beige solid (60 mg, 31%). LCMS (Method B): RT=2.65 min, M+H+=524.

Provenance & Evidence