(Pyrimidin-5-yl)boronic acid → 6-(pyrimidin-5-yl)-3-(4-piperidin-1-ylmethylphenyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole

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Reaction Conditions

Reaction Steps

A mixture of 6-chloro-3-(4-piperidin-1-ylmethylphenyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole (40 mg, 0.08 mmol), pyrimidin-5-yl boronic acid (20 mg, 0.16 mmol), 1,1′-[bis(diphenylphosphino)ferrocene]dichloropalladium(II) (3.2 mg, 0.004 mmol) in saturated aqueous sodium carbonate solution (0.15 mL) and acetonitrile (1.50 mL) was heated under microwave irradiation at 130° C. for 30 minutes. The cooled reaction mixture was diluted with DCM (20 mL) and methanol (2 mL) and washed with water (15 mL). The organic phase was separated, dried over sodium sulfate, filtered and evaporated in vacuo to afford a residue that 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/orange solid (10 mg, 23%). 1H NMR (DMSO-D6, 400 MHz): 12.44 (s, 1H), 9.52 (s, 2H), 9.21 (s, 1H), 9.08 (d, J=1.7 Hz, 2H), 9.02 (d, J=2.2 Hz, 1H), 8.96 (d, J=2.2 Hz, 1H), 7.77 (d, J=8.2 Hz, 2H), 7.46 (d, J=8.1 Hz, 2H), 3.50 (s, 2H), 2.37 (s, 4H), 1.53 (m, 4H), 1.41 (m, 2H). LCMS (Method D): RT=6.84 min, M+H+=421.

Provenance & Evidence