Neopentyl alcohol → HCID 89783444, compound

Participants

Reaction Conditions

Reaction Steps

NaH (60% w/w in mineral oil; 37.8 mg, 0.945 mmol) was added to a solution of neopentyl alcohol (Aldrich; 0.103 mL, 0.945 mmol) in DMF (1.0 mL), and the resulting suspension was stirred at 25° C. for 10 min. 2-(3-Fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 126; 40 mg, 0.135 mmol) was added, and the resulting solution was heated at 100° C. for 17 h. The mixture was cooled to 25° C., diluted with half-saturated aq. NH4Cl (30 mL), and extracted with DCM (2×40 mL). The combined organic extracts were washed with water (40 mL), dried over Na2SO4, filtered, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0-100% EtOAc/hexanes, then 0-10% MeOH/DCM) furnished 2-(2-methyl-3-(neopentyloxy)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (15.3 mg, 0.042 mmol, 31% yield) as a yellow solid: 1H NMR (400 MHz, CDCl3) δ ppm 12.03 (1H, br. s.), 8.00 (1H, d, J=7.6 Hz), 7.79 (1H, d, J=8.0 Hz), 7.56 (1H, t, J=7.8 Hz), 7.18 (1H, d, J=2.0 Hz), 5.43 (1H, br. s.), 4.12 (2H, s), 3.68 (2H, td, J=6.5, 1.4 Hz), 2.96 (2H, t, J=6.8 Hz), 2.71 (3H, s), 1.18 (9H, s). m/z (ESI, +ve) 365.1 (M+H)+.

Provenance & Evidence