Potassium Phosphate, Tribasic → HCID 24986679, compound

Participants

Reaction Steps

2-bromo-5,6,7,8-tetrahydro-6,6-dimethyl thiazolo[5,4-c]azepin-4-one (200 mg, 1.0 Eq.), 2-chloropyridine-4-boronic acid (126 mg, 1.1 Eq.), Pd2(DBA)3 (27 mg, 0.04 Eq.), K3PO4 (341 mg mg, 2.2 Eq.), were suspended/dissolved in H2O/dioxane (0.5 mL/2.5 mL) and degassed (vacuum/N2 cycles×5). Tricyclohexyl phosphine (20 mg, 0.1 Eq.) was then added, and the reaction mixture was 60° C. overnight. The reaction mixture was allowed to cool to RT, partitioned between EtOAc/H2O, and then filtered through celite. The aqueous layer was diluted with sat. Na2CO3 and extracted into EtOAc (3×50 mL). The combined organic layers were washed with brine (1×50 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. Purification was achieved using column chromatography (100% EtOAc), followed by tritration in Et2O. The precipitate was then washed with pentane. The title compound was obtained as a light yellow solid (74.1 mg, 33% yield); 1H NMR (DMSO D6) 1.0 (6H, s), 3.0 (4H, m), 7.9 (1H, m), 8.0 (1H, s), 8.8 (1H, br m), 9.1 (1H, m); LC/MS M+1; (obs.) 308.1; LC/MS M−1 (obs.) 306.3.

Provenance & Evidence