Hydrochloric Acid → HCID 86727229, compound

Participants

Reaction Conditions

Reaction Steps

In a 5 mL microwave vial, 1-(4-bromo-2-fluorobenzyl)-1H-indole-3-carboxylic acid (70 mg, 0.20 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (90 mg, 0.43 mmol), cesium carbonate (250 mg, 0.77 mmol), and Pd(dppf)Cl2 (20 mg, 0.02 mmol) was massed. The vial was then charged with a stir bar and 3 mL of 5:1 THF/H2O. The vial was capped and heated to 150° C. for 30 min. The reaction was cooled to ambient temperature and deemed to be complete by LCMS. The reaction mixture was diluted with H2O (20 mL) and dichloromethane (20 mL), and the organic layer was acidified to pH 1 with 1M HCl. The aqueous layer was extracted with dichloromethane (3×20 mL). The organic layers were combined, dried over MgSO4, filtered, and concentrated in vacuo. The crude material was purified by silica gel chromatography eluting with hexanes/ethyl acetate (0 to 100%) to afford 1-(2-fluoro-4-(1-methyl-1H-pyrazol-4-yl)benzyl)-1H-indole-3-carboxylic acid (LCMS: M+H=350, RT=0.687 min).

Provenance & Evidence