Tetrahydrofuran → HCID 60026346, compound

Participants

Reaction Conditions

Reaction Steps

2-[4-(5-Chloro-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1H-pyrrolo[3,2-b]pyridine-5-carbonitrile (50 mg, 0.11 mmol) was dissolved in 3 mL of THF. Isopropyl magnesium chloride (2 M in THF, 0.15 mL, 0.3 mmol) was added, followed by CuBr (7 mg, 0.05 mmol). The reaction was stirred at reflux (75° C.) for 30 minutes. The mixture was cooled to room temperature. The reaction was quenched with 1 mL of water, followed by 3 drops of concentrated HCl. The mixture was stirred for 10 minutes, and neutralized with saturated sodium carbonate solution until the pH was 8. The reaction mixture was extracted with ethyl acetate and washed with brine. The solvent was removed in vacuo. The residue was purified by preparative HPLC (medium polar condition) to give the title compound (39 mg, 70% yield).

Provenance & Evidence