5-bromo-1-(4-fluorophenyl)-1H-indazole → HCID 24958372, compound

Participants

Reaction Steps

To a chilled (−78° C.) solution of 5-bromo-1-(4-fluorophenyl)-1H-indazole (94 mg, 0.32 mmol, 1.1 equiv.) in 1.5 mL of THF was added n-BuLi (2.5 M in hexanes, 0.13 ml, 0.32 mmol, 1.1 equiv.) followed by a chilled (−78° C.) solution of 5-allyl-3-methyl-7-(2,2,2-trifluoro-acetyl)-3,5-dihydropyrrolo[3,2-d]pyrimidin-4-one (83 mg, 0.29 mmol, 1 equiv.) in 1 mL of THF. After 15 minutes, the mixture was quenched with water, warmed to room temperature, diluted with brine, and extracted with EtOAc. The combined organic layers were dried, filtered, and concentrated in vacuo. The residue was purified by flash chromatography using EtOAc-hex (0-60% gradient) to provide 44 mg (30%) of the title compound as a yellow foam. MS m/z 498.31 (MH+).

Provenance & Evidence