Sodium Carbonate → HCID 59557789, compound

Participants

Reaction Conditions

Reaction Steps

2-bromo-5,6,7,8-tetrahydro-7,7-dimethylthiazolo[5,4-c]azepin-4-one (200 mg, 1.0 Eq.), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (224 mg, 1.5 Eq.), Pd(DBA)2 (42 mg, 0.1 Eq.) and sodium carbonate (2M aq., 1090 μl, 3.0 Eq.) were suspended/dissolved in dioxane (4 mL). The system was degassed using vacuum/N2 cycles three times. P(tBu)3 (42 mg, 0.1 Eq.) was then added and the reaction mixture stirred at 80° C. overnight. The reaction mixture was allowed to cool to room temperature. The reaction mixture was partitioned in EtOAc/H2O and filtered through celite, which was washed copiously with EtOAc/H2O. The filtrate was partitioned and the aqueous was extracted with EtOAc (3×20 mL). The combined organics were washed with sat. aq. Na2CO3 (1×20 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by column chromatography (5% MeOH/95% EtOAc, followed by recrystallization from EtOAc/Hexanes gave the title compound was isolated as a brown powder (19.6 mg, 10% yield); 1H NMR (DMSO D6) 1.0 (6H, s), 3.0 (4H, m), 7.7-7.8 (2H, d), 8.3 (1H, br m), 8.7-8.8 (2H, d); LC/MS M+1 (obs.) 274.60; LC/MS M−1 (obs.) 272.80.

Provenance & Evidence