9-Benzenesulfonyl-3-bromo-5-[1-(2-hydroxyethyl)-piperidin-4-yloxy]-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile → HCID 67248027, compound

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Reaction Steps

A suspension of 9-benzenesulfonyl-3-bromo-5-[1-(2-hydroxyethyl)-piperidin-4-yloxy]-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (283 mg, 0.51 mmol) and palladium on carbon (10 wt %, 50 mg) in industrial methylated spirits (3 mL) and dichloromethane (3 mL) was stirred at ambient temperature under an atmosphere of hydrogen for 48 hours. The reaction vessel was purged with nitrogen then the reaction mixture was filtered through a PTFE filter cup. The filtrate was evaporated in-vacuo and the resultant residue purified by flash chromatography (silica, 24 g column, ISCO, 0-30% methanol in dichloromethane) to afford the title compound as an off-white solid (125 mg, 51%). 1H NMR (300 MHz, CDCl3): 9.59 (s, 1H), 8.76 (dd, J=4.9, 1.7 Hz, 1H), 8.54 (dd, J=7.9, 1.7 Hz, 1H), 8.27-8.26 (m, 2H), 7.62-7.61 (m, 1H), 7.56-7.44 (m, 3H), 5.04-5.03 (m, 1H), 3.70 (t, J=5.2 Hz, 2H), 3.09-3.09 (m, 2H), 2.69 (t, J=5.2 Hz, 2H), 2.51 (t, J=11.0 Hz, 2H), 2.32-2.25 (m, 2H), 2.12-2.10 (m, 2H).

Provenance & Evidence