HCID 58365196, compound → HCID 58364993, compound

Participants

Reaction Steps

A solution of 3-bromo-5-(1-tert-butoxycarbonyl-piperidin-4-yloxy)dipyrido[2,3-b;4′,3′-d]pyrrole-9-carboxylic acid benzyl ester (0.34 g, 0.59 mmol) in triflouroacetic acid (2 mL) and dichloromethane (4 mL) was allowed to stir at ambient temperature for 15 minutes. The solvent was evaporated and the resultant residue was treated with saturated sodium hydrogen carbonate solution (20 mL) and extracted with dichloromethane (3×30 mL). The combined organic phase was dried (Na2SO4), filtered and evaporated to afford a residue. The resultant residue was purified by flash chromatography (silica, 12 g cartridge, ISCO, 0-10% methanol in dichloromethane then 10% 2M NH3 in methanol in dichloromethane). The appropriate fractions were combined and evaporated to afford the title compound as a yellow solid (118 mg, 42%). LCMS (Method B): RT=3.13 min, M+H+=481/483. 1H NMR (400 MHz, CDCl3): 9.22 (s, 1H), 8.77 (d, J=2.3 Hz, 1H), 8.62 (d, J=2.4 Hz, 1H), 8.31 (s, 1H), 7.60-7.59 (m, 2H), 7.40-7.40 (m, 3H), 5.63 (s, 2H), 4.86-4.82 (m, 1H), 3.26-3.25 (m, 2H), 2.95-2.94 (m, 2H), 2.29-2.25 (m, 2H), 1.99-1.97 (m, 2H).

Provenance & Evidence