Sodium Carbonate → 4-tert-butyl-N-(5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-yl)benzamide

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Reaction Conditions

Reaction Steps

The titled compound was prepared using a procedure analogous to that described in connection with 9 (Example 9). To a microwave vial, N-(5-bromothiazolo[5,4-b]pyridin-2-yl)-4-tert-butylbenzamide (4A, 120 mg, 1.0 equivalent) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1.2 equivalent) in dioxane (0.17 M) and DMF (0.51 M) was stirred in N2. Followed by addition of Na2CO3 (2 M aqueous solution, 8.0 equivalents) and PdCl2(dppf)/DCM adduct (0.05 equivalent). The mixture was heated at 120° C. for 10 minutes. After cooling to room temperature, the crude mixture was added saturated aqueous NaHCO3 and extracted with EtOAc twice. Combined organic layers were dried over Na2SO4, filtered and concentrated. The crude product was purified by chromatography (SiO2, gradient of 1 to 10% MeOH/CH2Cl2) to give the titled compound 10 (50%) as a tan solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.33 (s, 9H) 7.61 (d, J=8.59 Hz, 2H) 8.08-8.16 (m, 4H) 8.27 (d, J=1.77 Hz, 2H) 8.72 (d, J=6.06 Hz, 2H) 13.07 (s, 1H); ESI-MS: m/z 389.0 (M+H)+.

Provenance & Evidence