Triphenylphosphine → HCID 58365196, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-bromo-5-hydroxy-dipyrido[2,3-b;4′,3′-d]pyrrole-9-carboxylic acid benzyl ester (234 mg, 0.59 mmol), 4-hydroxypiperidine-1-carboxylic acid tert-butyl ester (295 mg, 1.47 mmol) and triphenylphosphine (390 mg, 1.47 mmol) in anhydrous THF (7 mL) was treated dropwise with diethyl azodicarboxylate (295 mg, 1.47 mmol). On complete addition the mixture was heated at 50° C. for 1 hour. The mixture was concentrated in-vacuo and the resultant residue was purified by flash chromatography (silica, 12 g cartridge, ISCO, 0-7% methanol in dichloromethane). The appropriate fractions were collected and evaporated to afford the title compound as an orange oil (0.34 g, 100%). LCMS (Method B): RT=4.76 min, M+H+=581/583. 1H NMR (400 MHz, CDCl3): 9.27 (s, 1H), 8.80 (d, J=2.3 Hz, 1H), 8.61 (d, J=2.3 Hz, 1H), 8.32 (s, 1H), 7.60 (d, J=7.3 Hz, 2H), 7.43-7.36 (m, 3H), 5.64 (s, 2H), 4.89 (m, 1H), 3.40-3.39 (m, 2H), 3.02 (ddd, J=13.5, 9.8, 3.4 Hz, 2H), 2.21-1.80 (m, 4H), 1.46 (s, 9H).

Provenance & Evidence