Sodium Methoxide → N-isopropyl-5-(3-(4-methoxypyrimidin-2-yl)-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine

Participants

Reaction Conditions

Reaction Steps

A glass microwave reaction vessel was charged with 5-(3-(4-chloropyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-N-isopropyl-1,3,4-oxadiazol-2-amine (50 mg, 0.098 mmol) and sodium methoxide (18.57 mg, 0.344 mmol, Alfa Aesar) in MeOH (1 mL). The reaction was stirred and heated in a Initiator microwave reactor at 85° C. for 30 min and 100° C. for 1 h. The solvent was removed and the residue was purified with RP-HPLC (eluent: 10-50% MeCN in water with 0.1% TFA). The fractions containing the product were combined and concentrated to remove AcCN. The remaining mixture was neutralized with NH4OH and filtered and dried to give N-isopropyl-5-(3-(4-methoxypyrimidin-2-yl)-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (21.0 mg, 0.060 mmol, 61.0%) as an off-white solid. MS (ESI, pos. ion) m/z: 351.0 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.98 (1H, br. s.), 9.04 (1H, s), 8.52 (1H, d, J=5.7 Hz), 8.32 (1H, s), 7.69 (1H, d, J=8.6 Hz), 7.58 (2H, dd, J=13.4, 7.9 Hz), 6.68 (1H, d, J=5.7 Hz), 4.09 (3H, s), 3.66-3.82 (1H, m), 1.23 (6H, d, J=6.5 Hz)

Provenance & Evidence