tert-Butanol → HCID 59497230, compound

Participants

Reaction Steps

To a solution of 3-[3-(6-bromo-1-methyl-1H-indol-4-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid (71 mg, 0.15 mmol) in THF (11 mL) was added t-BuOH (1 mL). A solution of NBS (58 mg, 0.32 mmol) in THF (0.5 mL) was added and the resulting mixture was stirred at ambient temperature for 15 m, concentrated and used directly. This crude intermediate was dissolved in acetic acid (1.5 mL). Zn powder (70 mg, 1.1 mmol) was added and the resulting mixture was agitated for 15 m. The reaction mixture was filtered and the mother liquors were concentrated and purified directly by preparative HPLC using an acetonitrile/water/formic acid gradient to provide 12 mg (25%) of the title compound. LCMS (ESMS): m/z 486.88 (M+H).

Provenance & Evidence