Sodium Bicarbonate → HCID 178505849, compound

Participants

Reaction Conditions

Reaction Steps

1-Acetyl-3-[4-(4-fluorophenyl)piperazin-1-ylmethyl]-1H-indazole (112 mg, 0.32 mmol) in MeOH (3 mL) was treated with sodium methoxide (50 mg) and stirred for 1 h at 20° C. The mixture was poured into saturated aqueous sodium bicarbonate solution (5 mL) and extracted with CH2 Cl2 (3×5 mL). The combined organic extracts were dried (MgSO4), concentrated and the residue purified by flash chromatography (10→100% EtOAc in hexane) to give the title compound as a white solid (52 mg, 52%); mp 191°-192 ° C. (from CH2Cl2 /hexane); 1H NMR (360 MHz, d6 -DMSO) δ12.85 (bs, 1H, NH), 7.88 (d, J=8.9 Hz, 1H, indazole), 7.49 (d, J=8.9 Hz, 1H, indazole), 7.33 (t, J=8.9 Hz, 1H, indazole), 7.09 (t, J=8.9 Hz, 1H, indazole), 7.00 (m, 2 H, Ph), 6.92 (m, 2H, Ph), 3.89 (s, 2H, Ar--CH2N), 3.06 (m, 4H, piperazine), 2.58 (m, 4H, piperazine); MS (CI+) m/e 311 M+H+); Anal. calcd for C18H19N4F.1/4 H2O: C, 68.66; H, 6.24; N, 17.79. Found: C, 68.75; H, 6.13; N, 17.74.

Provenance & Evidence