Acetic Acid → HCID 58365159, compound

Participants

Reaction Steps

Acetaldehyde (3M solution in dichloromethane, 0.16 mL, 0.48 mmol) was added to a mixture of 3-bromo-5-(piperidin-4-yloxy)-dipyrido[2,3-b;4′,3′-d]pyrrole-9-carboxylic acid benzyl ester (116 mg, 0.24 mmol), sodium triacetoxyborohydride (77 mg, 0.36 mmol) and acetic acid (17 OL, 0.29 mmol) in methanol (3 mL) and dichloromethane (1 mL) and the mixture stirred for 18 hours. The solvent was evaporated and the resultant residue diluted with saturated aqueous sodium hydrogen carbonate solution (20 mL) and extracted with dichloromethane (3×30 mL). The combined organic layer was dried (Na2SO4), filtered and evaporated to give a residue. The resultant residue was purified by flash chromatography (silica, 12 g cartridge, ISCO, 0-8% methanol in dichloromethane). The appropriate fractions were collected and evaporated to afford the title compound as a light yellow solid (75 mg, 61%). LCMS (Method B): RT=3.43 min, M+H+=509/511. 1H NMR (400 MHz, CDCl3): 9.23 (s, 1H), 8.77 (d, J=2.3 Hz, 1H), 8.62 (s, 1H), 8.31 (s, 1H), 7.60-7.60 (m, 2H), 7.40-7.40 (m, 3H), 5.63 (s, 2H), 4.85 (s, 1H), 2.91 (br s, 2H), 2.62 (br s, 2H), 2.33 (br s, 2H), 2.14 (br s, 2H), 1.59 (br s, 2H), 1.23 (br s, 3H).

Provenance & Evidence