Potassium Carbonate → HCID 86698807, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromo-6-chloro-1H-indazole-3-carboxylic acid (30.0 mg, 0.11 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (7.3 mg, 0.010 mmol) was purged with N2. To this mixture was added 2-[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-phenyl]-1,1,1-trifluoropropan-2-ol (35.0 mg, 0.12 mmol) in toluene (1.0 mL) and EtOH (0.5 mL), followed by 2N aqueous potassium carbonate solution (0.22 mL, 0.44 mmol). The reaction mixture was heated to 110° C. for 18 hours, cooled to room temperature and concentrated in vacuo. The resulting solid was partitioned between water and EtOAc, and acidified to pH 5 with aqueous 1N citric acid. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude material was purified by reverse phase HPLC (Column: Waters Sunfire C18 19×100 mm, 5 μm; Mobile phase A: 0.05% TFA in water (v/v); Mobile phase B: 0.05% TFA in MeCN (v/v); HOLD at 100.0% H2O/0.0% MeCN for 1.0 min. 100.0% H2O/0.0% MeCN linear to 5.0% H2O/95.0% MeCN in 6.75 min, linear to 0% H2O/100% MeCN to 7.0 min. HOLD at 0% H2O/100% MeCN from 7.0 to 8.0 min. Flow: 30 mL/min) to give the title compound (6.5 mg, 15% yield).

Provenance & Evidence