Sodium hydride → HCID 25100942, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (1H-indol-4-yl)-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]oct-6-yl)-methanone (82 mg, 0.27 mmol) in dry DMF (2 mL) at room temperature under an inert atmosphere of nitrogen was added sodium hydride (17 mg, 0.69 mmol, 60% dispersion in oil), and after stirring for 30 min ethyl bromopropionate (100 mg, 0.55 mmol) was added, and the reaction mixture was stirred for 72 h at 60° C. The reaction was quenched by the addition of water (20 mL) followed by extraction with DCM (3×50 mL). The combined organic phases were dried (MgSO4), filtered, and evaporated in vacuo. The resulting solid was purified by preparative HPLC, dried in vacuo at 50° C. affording 29 mg (27%) of the title compound as a solid. MS-ESI m/z 397; 1H NMR (400 MHz, DMSO) δ 0.88-1.08 (m, 6H), 1.14-1.22 (m, 7H), 1.28-1.29 (m) and 1.58-1.67 (m, 1H), 1.37-1.43 (m, 3H), 1.77-1.81 (m, 1H), 2.32-2.36 (m) and 3.10-3.20 (m, 1H), 2.81 (t, 2H), 3.35 (dd) and 3.75 (dd, 1H), 4.02-4.04 (m) and 4.68-4.70 (m, 1H), 4.11 (q, 2H), 4.46 (t, 2H), 6.44-6.50 (m, 1H), 7.10-7.13 (m, 1H), 7.17-7.26 (m, 2H), 7.38 (d, 1H).

Provenance & Evidence