Ethyl orthoformate → HCID 57618481, compound

Participants

Reaction Conditions

Reaction Steps

7-(4-Butyl-phenyl)-6-fluoro-5,10-dihydro-indeno[1,2-b]indol-2-ylamine (example 98, step 1, 60 mg, 0.1620 mmol) is dissolved in AcOH (1.6 mL). Triethyl orthoformate (38 mg, 0.2591 mmol, 1.6 eq.) and sodium azide (15 mg, 0.2429 mmol, 1.5 eq.) are added to the starting material solution sequentially at room temperature. The resulting reaction mixture is heated to 80° C. for 3.5 h. After cooling to room temperature, the reaction is diluted with EtOAc and sequentially washed with H2O, 1 N HCl (aq), and saturated aqueous NaCl. The organic solution is dried over Na2SO4 and concentrated. The resulting residue is purified by reverse phase HPLC to afford the title compound as a tan solid: 1H NMR (400 MHz, Acetone-d6) δ 11.31 (bs, 1H), 9.77 (s, 1H), 8.15 (s, 1H), 7.97 (s, 2H), 7.62-7.52 (m, 3H), 7.38 (d, 2H), 7.21 (dd, 1H), 3.99 (s, 2H), 2.69 (t, 2H), 1.72-1.63 (m, 2H), 1.50-1.40 (m, 2H), 0.99 (t, 3H); ESMS m/z 424.1 (M+H+).

Provenance & Evidence