Aluminium lithium hydride → HCID 178505446, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 6-fluoro-3-[4-(2-phenylacetyl)piperazin-1-ylmethyl]-1H-indazole (156 mg, 0.44 mmol) in THF (5 mL) was treated with LiAlH4 (0.44 mL of a 1.0M solution in THF, 0.44 mmol) and heated at 40° C. for 16 h. The solution was cooled, diluted with EtOAc (50 mL), 2M aqueous NaOH was added (200 mL) and the resulting suspension was stirred for 1 h at 20° C., filtered, concentrated and the residue purified by flash chromatography (EtOAc→10% MeOH in EtOAc) to give the title compound (130 mg, 87%) as a white solid; mp 148°-149° C. (from Et2O/hexane); 1H NMR (360 MHz, d6 -DMSO) δ12.85 (bs, 1H, NH), 7.89 (dd, J=8.9, 5.5 Hz, 1H, indazole), 7.28-7.14 (m, 6H, aromatic), 6.96 (dt, J=9.3, 2.2 Hz, 1H, indazole), 3.79 (s, 2H, Ar--CH2N), 2.70 (t, J=7.2 Hz, 2H, CH2 --Ph), 2.51-2.40 (m, 10H, piperazine, CH2); MS (CI+) m/e 339 (M+H+); Anal. calcd for C20H23FN4 : C, 70.98; H, 6.85, N, 16.56. Found: C, 71.35; H, 6.88; N, 16.56.

Provenance & Evidence