Ammonium Chloride → HCID 68283386, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-methoxy-3-(2-(4-nitro-1H-imidazol-1-yl)ethyl)-1H-indole in EtOH/H2O (1.8 mL/0.9 mL), NH4Cl (158 mg, 2.95 mmol) and Fe (99 mg, 1.77 mmol) was added. The resulting black mixture was heated to 85° C. for 30 min, then it was filtered while hot and the filter cake was rinsed with EtOH. The filtrate was concentrated in vacuo and the residue partitioned between DCM and aq. 1 N NaOH-solution. The org. layer was separated and the aq. layer wa extracted with DCM. The combined organic extracts were washed with brine, dried (MgSO4), filtered and the solvents were removed under reduced pressure to yield the title compound in mixture with 1-(2-(5-methoxy-1H-indol-3-yl)ethyl)-1H-imidazol-5-amine as a dark brown solid, which was used in the next step without further purification. LC-MS conditions A: tR=0.52 min, [M+H]+=257.22.

Provenance & Evidence