Water → 2-(6-(1-benzyl-1H-pyrazol-4-yl)-2H-benzo[b][1,4]oxazin-4(3H)-yl)-6,6-dimethyl-6,7-dihydrothiazolo[5,4-c]pyridin-4(5H)-one

Participants

Reaction Steps

A stirred solution of Example 39 (0.051 g, 0.129 mmol), 1-benzyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (0.049 g, 0.173 mmol), K2CO3 (0.054 g, 0.388 mmol), tetra-n-butylammonium bromide (0.124 g, 0.385 mmol), tetrakis-(triphenylphosphine)palladium(0) (0.010 g, 0.009 mmol) and H2O (0.5 mL) in THF (1 mL) was heated to 125° C. under microwave irradiation for 1 h. The reaction mixture was diluted with EtOAc and washed with water and brine. The organic fractions were dried (MgSO4), filtered and concentrated in vacuo. The crude material was triturated with Et2O to give the title compound (0.041 g, 68%) as a beige solid. δH (CDCl3) 8.03 (1H, d, J 1.9 Hz), 7.78 (1H, s), 7.60 (1H, s), 7.40-7.25 (5H, m), 7.18 (1H, dd, J 8.5 and J 2.1 Hz), 6.96 (1H, d, J 8.3 Hz), 5.37 (2H, s), 5.26 (1H, br. s), 4.38-4.32 (2H, m), 4.22-4.16 (2H, m), 2.89 (2H, s), 1.42 (6H, s). LCMS (ES+) 472.0 (M+H)+, RT 3.53 minutes (Method 1).

Provenance & Evidence