Sodium Carbonate → HCID 86706572, compound

Participants

Reaction Conditions

Reaction Steps

7-Chloro-4-hydroxy-6-iodo-3-(1H-pyrazol-1-yl)quinolin-2(1H)-one (Intermediate 112) (300 mg, 0.774 mmol), N-(4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)thiazol-2-yl) acetamide (Intermediate 31) (264 mg, 1.0 mmol), Pd(Ph3P)4 (8.94 mg, 7.74 μmol), 1M Na2CO3 (2.32 mL, 2.32 mmol) were mixed in 1,4-dioxane (3 mL). The reaction mixture was stirred at 120° C. for 1 h under microwave irradiation then cooled to room temperature and filtered through celite. The filtrate was diluted with water and extracted twice with DCM. The organic layers were combined, dried over Na2SO4 and concentrated under reduced pressure. The crude product was then diluted with EtOH and concentrated hydrochloric acid and the resulting mixture was heated at 90° C. overnight. The reaction mixture was cooled to room temperature then filtered. The powder was washed successively with water, EtOH and Et2O to afford the title compound 6-[4-(2-amino-1,3-thiazol-4-yl)phenyl]-7-chloro-4-hydroxy-3-(1H-pyrazol-1-yl)-2(1H)-quinolinone hydrochloride (70 mg, 19.1% yield) as a grey powder. LCMS: (M+H)+=436; Rt=2.14 min. HRMS: calculated for C21H13ClN5O2S (M−H)+: 434.0479. found: 434.0435.

Provenance & Evidence