Sodium Carbonate → 5-(1-Ethylpiperidin-4-yloxy)-3-isopropenyl-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

Participants

Reaction Conditions

Reaction Steps

9-Benzenesulfonyl-3-bromo-5-(1-ethyl-piperidin-4-yloxy)-9H-dipyrido[2,3-b:4′,3′-d]pyrrole-6-carbonitrile (147 mg, 0.272 mmol) and [1,1′-bis(diphenylphosphino) ferrocene]dichloropalladium(II) (11 mg, 0.014 mmol) were dissolved in THF (9 mL) and 1N aqueous sodium carbonate (3 mL) added followed by isopropenylboronic acid pinacol ester (0.076 mL, 0.408 mmol) and placed under an argon atmosphere. The reaction mixture was heated under microwave irradiation at 140° C. for 50 min. The cooled reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution (20 mL) and extracted into ethyl acetate (4×20 mL). The combined organic phase was washed with brine (20 mL), dried over sodium sulfate and concentrated in vacuo to afford the title compound as a brown solid (163 mg) which was used without further purification in the next step. 1H NMR (CDCl3, 300 MHz): 12.05 (br s, 1H), 8.81 (d, J=2.2 Hz, 1H), 8.77 (s, 1H), 8.64 (d, J=2.2 Hz, 1H), 5.48 (s, 1H), 5.28-5.24 (m, 1H), 5.09-4.97 (m, 1H), 3.02-2.91 (m, 2H), 2.49 (q, J=7.2 Hz, 2H), 2.35-2.20 (m, 7H), 2.19-2.07 (m, 2H), 1.12 (t, J=7.2 Hz, 3H).

Provenance & Evidence