Sodium Methoxide → HCID 66604677, compound

Participants

Reaction Steps

(8-Carbamoyl-6-(3,4-dichlorophenyl)-9H-carbazol-2-yl)methyl acetate (150 mg, 0.211 mmol, Example 139) was dissolved in a mixture of MeOH (3 mL) and DMF (6 mL). To this solution was added sodium methanolate (140 mg, 0.648 mmol) and the reaction left stirring for 0.5 h. The product was isolated by preparative HPLC (100×30 mm Luna C18 column, flow rate 42 ml permin, gradient elution starting with A:B=90:10 and ending with A:B=30:70 [A=10 mM NH4OAc in 5% aqueous acetonitrile; B=10 mM NH4OAc in 95% aqueous acetonitrile] over 20 min) followed by removal of solvent to afford 39 mg of 3-(3,4-dichlorophenyl)-7-(hydroxymethyl)-9H-carbazole-1-carboxamide as a light yellow solid. MS (ESI) m/z 383.1 (M−H). 1H NMR (DMSO-d6) δ ppm 11.44 (1H, s), 8.73 (1H, d, J=1.53 Hz), 8.36 (1H, br. s.), 8.30 (1H, d, J=1.53 Hz), 8.22 (1H, d, J=2.14 Hz), 8.19 (1H, d, J=7.93 Hz), 7.94 (1H, dd, J=8.55, 2.14 Hz), 7.77 (1H, d, J=8.24 Hz), 7.71 (1H, s), 7.56 (1H, br. s.), 7.18 (1H, d, J=7.93 Hz), 5.24 (1H, t, J=5.80 Hz), 4.66 (2H, d, J=5.80 Hz).

Provenance & Evidence