2-Bromopropane → HCID 136338254, compound

Participants

Reaction Steps

To a stirred solution of 5-(5-(6-isopropoxypyrazin-2-yl)-1H-indol-3-yl)-1,3,4-oxadiazol-2(3H)-one (0.2 g, 0.5 mmol) and 2-bromo propane (0.08 g, 0.6 mmol) in DMF (1 mL) at 0° C. was added 60% sodium hydride (in mineral oil) (0.040 g, 0.1 mmol) and the reaction was stirred for 2 h at RT. The reaction was quenched with water (25 mL) and extracted with EtOAc (25 mL). The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified with silica gel chromatography (eluting with 20% EtOAc in hexanes) to give 5-(5-(6-isopropoxypyrazin-2-yl)-1H-indol-3-yl)-3-isopropyl-1,3,4-oxadiazol-2(3H)-one (50 mg, 22%) as a white solid. MS (ESI, pos. ion) m/z: 380.0 (M+1); 1H NMR (400 MHz, CDCl3): δ ppm 8.86 (br s, 1H), 8.70 (s, 1H), 8.67 (s, 1H), 8.09 (s, 1H), 8.01 (dd, J=8.4, 1.6 Hz, 1H), 7.78 (d, J=2.8 Hz, 1H), 7.56 (d, J=8.4 Hz, 1H), 5.51-5.57 (m, 1H), 4.42-4.49 (m, 1H), 1.50 (d, J=6.8 Hz, 6H), 1.48 (d, J=6.4 Hz, 6H).

Provenance & Evidence