4-(1-Piperidylmethyl)phenylboronic Acid → HCID 58266504, compound

Participants

Reaction Conditions

Reaction Steps

A degassed mixture of tert-butyl-{3-Bromo-9H-dipyrido[2,3-b;4′,3′-d]pyrrol-6-yl}-carbamate (105 mg, 0.290 mmol), 4-piperidin-1-ylmethyl-phenyl boronic acid (73.7 mg, 0.336 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (17.8 mg, 2.18 μmol, 7.5 mol %) in acetonitrile (1.3 mL) and 1M aqueous potassium acetate (1.3 mL) was heated under microwave irradiation at 140° C. for 30 minutes. The cooled reaction mixture was diluted with 20% MeOH in DCM and water, and filtered to remove the solids. The filtrate layers were separated and the aqueous phase was extracted into 20% MeOH in DCM, and the combined organic phase concentrated in vacuo. The resultant residue was purified by preparative HPLC (0-30% MeCN in water (0.1% formic acid) over 30 min, 35 mL/min) to afford the title compound as a yellow solid (41 mg, 40%). 1H NMR (DMSO-D6, 400 MHz): 11.47 (s, 1H), 8.77 (d, J=2.0 Hz, 1H), 8.73 (d, J=2.0 Hz, 1H), 8.30 (s, 1H), 8.16 (s, 1H), 7.73 (d, J=8.1 Hz, 2H), 7.41 (d, J=8.1 Hz, 2H), 7.18 (s, 1H), 3.48 (s, 2H), 2.38 (m, 4H), 1.57-1.47 (m, 4H), 1.41 (m, 2H). LCMS (Method D): RT=6.20 min, M+H+=358.

Provenance & Evidence