Morpholine → 2-(4-Methoxy-phenyl)-5-morpholin-4-yl-oxazolo[5,4-b]pyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-chloro-2-(4-methoxy-phenyl)-oxazolo[5,4-b]pyridine (25 mg, 0.096 mmol) in DMSO (1 mL) was added L-proline (11.04 mg, 0.096 mmol), CuI (18.27 mg, 0.096 mmol), morpholine (13 μL, 0.15 mmol) and K3PO4 (40.7 mg, 0.192 mmol). The reaction vessel was sealed and heated to 90° C. overnight, at which point the reaction was diluted with water and extracted with EtOAc. The organics were concentrated leaving a residue that was purified by reverse phase chromatography to afford 2-(4-methoxy-phenyl)-5-morpholin-4-yl-oxazolo[5,4-b]pyridine (4.3 mg, 0.013 mmol, 14% yield). ES MS (M+H+)=312; 1H NMR (499 MHz, DMSO-d6): δ 8.07-8.02 (d, J=8.7 Hz, 2H); 7.98-7.94 (m, 1 H); 7.17-7.11 (d, J=8.7 Hz, 2H); 6.91 (d, J=8.8 Hz, 1H); 3.86 (s, 3H); 3.73 (t, J=4.8 Hz, 4H); 3.51 (t, J=4.8 Hz, 4H); HRMS m/z 312.1352 (C17H17N3O3+H+ requires 312.1343)

Provenance & Evidence