(E)-3-(2-(Dimethylamino)vinyl)-4-nitropyridine 1-oxide → 5-Azaindole

HRID 875398Notes

Reaction equation

HRID 875398 reaction equation
CN(C)/[CH:3]=[CH:4]/[C:5]1[CH:6]=[N+:7]([O-])[CH:8]=[CH:9][C:10]=1[N+:11]([O-])=O>CO.[Pd]>[NH:11]1[C:10]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[CH:4]=[CH:3]1

Participants

4

Reactant 1

HCID 11344817(E)-3-(2-(Dimethylamino)vinyl)-4-nitropyridine 1-oxide

Product 1

HCID 92205-AzaindoleYield 44%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a suspension of (E)-N,N-dimethyl-2-(4-nitro-1-oxidopyridin-3-yl)ethenamine (400 mg, Step c) in methanol was added palladium on carbon (50 mg, 10% wet) and the reaction mixture was stirred under hydrogen atmosphere for 2 hours. The reaction mixture was filtered through celite and the filtrate was concentrated to get 1H-pyrrolo[3,2-c]pyridine (98 mg, 44%) as off-white solid.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-5d99eec0d6d64e5fb9048986d64835a8
Source dataset
uspto-grants-2015_03
Patent number
US08980911B2

Reaction notes

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