Methanol → N-(4-methoxybenzyl)-5-(3-methyl-1H-indazol-5-yl)oxazol-2-amine

Participants

Reaction Conditions

Reaction Steps

A glass microwave reaction vessel was charged with 5-(2-iodooxazol-5-yl)-3-methyl-1H-indazole (0.40 g, 123 μmol), (4-methoxyphenyl)methanamine (1.13 mL, 8620 μmol) and NMP (2.0 mL). The reaction mixture was stirred and heated in a Smith Synthesizer® microwave reactor (Personal Chemistry, Inc., Upssala, Sweden) at 165° C. for 10 minutes. The crude product was adsorbed onto a plug of silica gel and chromatographed through two stacked Redi-Sep® pre-packed silica gel column (12 g), eluting with a gradient of 1% to 10% 2 M NH3.MeOH in DCM, to give N-(4-methoxybenzyl)-5-(3-methyl-1H-indazol-5-yl)oxazol-2-amine (422 mg, 98% yield). LCMS (API-ES) m/z (%): 355 (100%, M++H); 1H NMR (400 MHz, MeOH-d4) 7.76 (s, 1H) 7.52 (s, 1H) 7.48-7.57 (m, 1H) 7.38-7.46 (m, 1H) 7.26-7.34 (m, 2H) 6.96-7.02 (m, 1H) 6.80-6.91 (m, 2H) 4.42 (s, 2H) 3.75 (d, J=6.06 Hz, 3H) 3.30 (s, 3H).

Provenance & Evidence