2-Bromo-6-fluoropyridine → 2-{6-[(6-Bromopyridin-2-yl)oxy]-2,3-dihydro-4h-1,4-benzoxazin-4-yl}-6,6-dimethyl-6,7-dihydro[1,3]thiazolo[5,4-c]pyridin-4(5h)-one

Participants

Reaction Conditions

Reaction Steps

To a solution of Example 57 (50 mg, 0.151 mmol) in THF (4 mL) was added 2-bromo-6-fluoropyridine (53 mg, 0.302 mmol) and sodium tert-butoxide (58 mg, 0.604 mmol). The mixture was heated to 150° C. under microwave irradiation for 30 minutes then cooled to r.t. The resulting mixture was partitioned between DCM (50 mL) and water (50 mL); the organic phase was washed with brine (50 mL), dried (MgSO4), and concentrated in vacuo. The residue was triturated with Et2O to yield the title compound (10 mg, 14%) as an off-white solid. δH (CDCl3) 7.95 (1H, d, J 2.6 Hz), 7.52 (1H, t, J 7.9 Hz), 7.19 (1H, d, J 7.5 Hz), 6.97 (1H, d, J 8.9 Hz), 6.85 (1H, dd, J 8.9 and 2.6 Hz), 6.80 (1H, d, J 8.1 Hz), 5.32 (1H, s), 4.39-4.32 (2H, m), 4.16-4.10 (2H, m), 2.86 (2H, s), 1.38 (6H, s). LCMS (ES+) 487.0 (M+H)+, RT 3.73 minutes (Method 1).

Provenance & Evidence