Nitromethane → 2-Methoxy-10-[2-nitroethenyl]-6,7,8,9-tetrahydropyrido[2,3-b]indolizine

Reaction equation

BrC1C=C[CH:17]=[CH:16][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[N:9][C:10]([O:14][CH3:15])=[CH:11][CH:12]=2)[CH:7]=[CH:6]1.[C:20]([O-])(=O)[CH3:21].[NH4+].[N+:25](C)([O-:27])=[O:26]>>[CH3:15][O:14][C:10]1[CH:11]=[CH:12][C:13]2[N:5]3[C:6]([CH2:17][CH2:16][CH2:3][CH2:4]3)=[C:7]([CH:21]=[CH:20][N+:25]([O-:27])=[O:26])[C:8]=2[N:9]=1

Participants

Reactant 3

HCID 6375Nitromethane

HCID 517165Ammonium Acetate

HCID 178207361-(2-Bromobenzyl)-5-methoxy-1H-pyrrolo[3,2-b]pyridine

Product 1

HCID 694179332-Methoxy-10-[2-nitroethenyl]-6,7,8,9-tetrahydropyrido[2,3-b]indolizine

Procedure

550 mg (2.39 mmol) of the compound obtained in Step C dissolved in 25 ml of nitromethane are heated at 120° C., for 3 hours in the presence of 460 mg (5.97 mmol) of ammonium acetate. After returning to room temperature and evaporation to dryness, the reaction mixture is diluted in dichloromethane and washed with water. The organic phase is dried over magnesium sulphate, filtered and evaporated. After washing with a pentane/diethyl ether mixture, the title compound is obtained in the form of a brown solid.