Benzyl Alcohol → HCID 59375144, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 8-carbamoyl-5-(2-fluorophenyl)-9H-carbazole-2-carboxylic acid (Example 23-2, 320 mg, 0.919 mmol) and 4 Å molecular sieves (60 mg) in 1,4-dioxane (15 mL) at 50° C. was treated with TEA (0.316 mL, 2.269 mmol) and diphenylphosphoryl azide (0.491 mL, 2.269 mmol). The mixture was stirred at 50° C. for 1.5 h, followed by addition of phenylmethanol (0.951 mL, 9.19 mmol). The mixture was then stirred at 80° C. for 18 h. The cooled mixture was partitioned between EtOAc and NaHCO3 (aq). The organic phase was washed with brine, dried and concentrated The residue was purified by column chromatography (eluting with 35:65 hexane-EtOAc). The residue after concentration was suspended in hexane and the precipitate was collected by filtration to provide benzyl 8-carbamoyl-5-(2-fluorophenyl)-9H-carbazol-2-ylcarbamate as an off-white solid (400 mg, 83%). 1H NMR (400 MHz, DMSO-d6) δ 11.50 (s, 1 H) 9.83 (s, 1 H) 8.15 (br. s., 1 H) 8.00 (s, 1 H) 7.91 (d, J=7.69 Hz, 1 H) 7.45-7.64 (m, 3 H) 7.32-7.46 (m, 7 H) 7.03 (d, J=7.91 Hz, 1 H) 6.87-6.98 (m, 2 H) 5.15 (s, 2 H). Mass spectrum m/z 454.1 (M+H)+.

Provenance & Evidence