Water → 6,6-Dimethyl-2-[6-(2-methoxy-6-methylpyridin-3-yl)-2,3-dihydro-4h-1,4-benzoxazin-4-yl]-6,7-dihydro[1,3]thiazolo[5,4-c]pyridin-4(5h)-one

Participants

Reaction Conditions

Reaction Steps

To a suspension of Example 39 (100 mg, 0.254 mmol) in THF (3 mL) and water (1 mL) was added tetra-n-butylammonium bromide (164 mg, 0.509 mmol), sodium carbonate (54 mg, 0.509 mmol), 2-methoxy-6-methylpyridine-3-boronic acid (85 mg, 0.509 mmol) and tetrakis(triphenylphosphine)palladium(0) (catalytic amount). The reaction was heated at 120° C. under microwave irradiation for 20 minutes. The resulting mixture was partitioned between DCM (50 mL) and water (50 mL); the organic fraction was washed with brine (50 mL), dried (MgSO4), and concentrated in vacuo. The residue was purified by preparative HPLC (Method 6) to yield the title compound (28 mg, 25%) as a beige solid. δH (CDCl3) 8.06 (1H, d, J 1.9 Hz), 7.50 (1H, d, J 7.3 Hz), 7.26 (1H, dd, J 8.5 and 2.1 Hz), 6.99 (1H, d, J 8.5 Hz), 6.81 (1H, d, J 7.5 Hz), 5.22 (1H, br. s), 4.39-4.31 (2H, m), 4.26-4.19 (2H, m), 4.00 (3H, s), 2.87 (2H, s), 2.49 (3H, s), 1.39 (6H, s). LCMS (ES+) 437.0 (M+H)+, RT 3.99 minutes (Method 1).

Provenance & Evidence