Morpholine → HCID 10194087, compound

Participants

Reaction Conditions

Reaction Steps

2-[4-(6-bromopyridin-2-yl)-3-methoxyphenyl]-1,3-benzoxazole (150 mg, 0.39 mmol), morpholine (41 μL, 0.47 mmol), Pd2(dba)3 (8.2 mg, 0.0078 mmol), BINAP (9.8 mg, 0.016 mmol), and NaOtBu (53 mg, 0.55 mmol) were combined in a sealable tube evacuated and backfilled with argon. Toluene (4 mL) was added and the mixture was degassed with a stream of argon for 5 min. The tube was sealed and the mixture was heated to 70° C. for 18 h. Crude mixture was adsorbed onto silica gel and purified by automated flash chromatography using an EtOAc/hexanes gradient to afford the desired 2-[3-methoxy-4-(6-morpholin-4-ylpyridin-2-yl)phenyl]-1,3-benzoxazole as an orange solid: 1H NMR (CDCl3, 300 MHz) δ 8.07–8.05 (d, 1H), 7.96–7.95 (m, 1H), 7.88 (s, 1H), 7.83–7.78 (m, 1H), 7.65–7.58 (m, 2H), 7.42–7.36 (m, 3H), 6.65–6.62 (d, 1H), 4.02 (s, 3H), 3.88–3.85 (t, 4H), 3.61–3.58 (t, 4H). MS (ESI) 388 (M+H)+.

Provenance & Evidence