Nitrogen → HCID 25070281, compound

Participants

Reaction Steps

A solution of tert-butyl 6-methyl-1-(phenylsulfonyl)-7-{[(trifluoromethyl)sulfonyl]oxy}-1,3,4,6-tetrahydro-5H-azepino[5,4,3-cd]indole-5-carboxylate, Intermediate 16 (16 mg, 0.028 mmol) in MeOH (4 mL) and was carefully added to a 16 mm test tube containing Pd/C (35 mg). The suspension was purged with N2, ammonium formate (88 mg, 1.4 mmol) was added in one portion, the mixture was N2-purged once more and the mixture was stirred at room temperature over two days. The detriflated intermediate was purified with preparative HPLC (ACE C8 5 mm, water containing 0.1% TFA —CH3CN). The pure fraction was evaporated at reduced pressure, DCM/TFA 50/50, (1 mL) was added and the mixture was left at room temperature for one hour. The crude was purified by preparative HPLC (Xterra C18, 10 mM NH4CO3 (pH 10)-CH3CN) to give 0.8 mg of the title compound as a white oil. MS (ESI) m/z 326 [M+H]+.

Provenance & Evidence