Methanol → N-(4-methoxybenzyl)-5-(isoquinolin-6-yl)oxazol-2-amine

Participants

Reaction Conditions

Reaction Steps

A glass microwave reaction vessel was charged with 6-(2-iodooxazol-5-yl)isoquinoline (0.10 g, 310 μmol), (4-methoxyphenyl)methanamine (0.28 mL, 217 μmol) and NMP (2.00 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 residual 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% of 2 M NH3.MeOH in DCM to provide N-(4-methoxybenzyl)-5-(isoquinolin-6-yl)oxazol-2-amine (98 mg, 95% yield). LCMS (API-ES) m/z (%): 332.1 (100%, M++H); 1H NMR (400 MHz, MeOH-d4) δ ppm 9.12 (s, 1H) 8.38 (d, J=5.87 Hz, 1H) 8.04 (d, J=8.80 Hz, 1H) 7.94 (s, 1H) 7.84 (dd, J=8.61, 1.56 Hz, 1H) 7.76 (d, J=5.87 Hz, 1H) 7.42 (s, 1H) 7.33 (d, J=8.80 Hz, 2H) 6.90 (d, J=8.61 Hz, 2H) 4.47 (s, 2H) 3.77 (s, 3H).

Provenance & Evidence