Triacetoxyperiodinane → HCID 86642954, compound

Participants

Reaction Steps

Step 1 A partial solution of 4-bromo-7-(hydroxymethyl)-9H-carbazole-1-carboxamide (Example 30-2, 1.00 g, 3.13 mmol) in THF (75 mL) was stirred at rt and treated with 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1 H)-one (Dess-Martin periodinane, 1.993 g, 4.70 mmol). After 45 min, the solution was diluted with EtOAc and washed with 5% aqueous sodium sulfite, NaHCO3 (aq), and brine, then was dried and concentrated. The residue was triturated with methanol, and the precipitate was collected by filtration, washed with methanol and dried to provide 4-bromo-7-formyl-9H-carbazole-1-carboxamide as a tan powder (ca. 85% purity, 948 mg, 81%) used without purification. 1H NMR (400 MHz, DMSO-d6) δ 12.13 (1 H, s), 10.14 (1 H, s), 8.80 (1 H, d, J=8.1 Hz), 8.38 (1 H, d, J=0.9 Hz), 8.28 (1 H, br. s.), 7.97 (1 H, d, J=8.1 Hz), 7.83 (1 H, dd, J=8.3, 1.4 Hz), 7.64 (1 H, br. s.), 7.54 (1 H, d, J=8.1 Hz). Mass spectrum m/z 317, 319 (M+H)+.

Provenance & Evidence