HCID 67155953, compound → HCID 67155998, compound

HRID 2196703Notes

Reaction equation

HRID 2196703 reaction equation
[CH3:1][N:2]([CH3:15])[C:3]1[C:11]2[C:6](=[N:7][CH:8]=[C:9]([N+:12]([O-])=O)[CH:10]=2)[NH:5][CH:4]=1.[H][H]>CO.CCOC(C)=O.[Pd]>[CH3:1][N:2]([CH3:15])[C:3]1[C:11]2[C:6](=[N:7][CH:8]=[C:9]([NH2:12])[CH:10]=2)[NH:5][CH:4]=1

Participants

6

Reactant 2

HCID 67155953HCID 67155953, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67155998HCID 67155998, compoundYield 40%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

N,N-Dimethyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-3-amine (50 mg) was taken up in methanol (3 mL) and EtOAc (3 mL). 10% Pd/C (50 mg) was added, and the mixture was hydrogenated under a balloon of hydrogen for one hour. The mixture was then filtered through GF/F filter paper, and the filtrate was concentrated to a solid. This material was purified by preparative TLC (0.5 mm plate, 10% MeOH/DCM/0.5% NH4OH) to give N3,N3-dimethyl-1H-pyrrolo[2,3-b]pyridine-3,5-diamine (17 mg, 40%). (APCI-pos) M+1=177.2.

Workup

  1. filtrationThe mixture was then filtered through GF/F
  2. filtrationfilter paper
  3. concentrationthe filtrate was concentrated to a solid
  4. customThis material was purified by preparative TLC (0.5 mm plate, 10% MeOH/DCM/0.5% NH4OH)

Sources & evidence

ORD record
ord-6f6307912b974b5ead69b68abd5e3182
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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