HCID 57908191, compound → HCID 57908158, compound

HRID 1044007Notes

Reaction equation

HRID 1044007 reaction equation
[C:1]([C:5]1[NH:16][C:8]2=[N:9][CH:10]=[C:11]([N+:13]([O-])=O)[CH:12]=[C:7]2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Ni]>[C:1]([C:5]1[NH:16][C:8]2=[N:9][CH:10]=[C:11]([NH2:13])[CH:12]=[C:7]2[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 57908191HCID 57908191, compound

Product 1

HCID 57908158HCID 57908158, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of 2-tert-butyl-5-nitro-1H-pyrrolo[2,3-b]pyridine (2.3 g, 0.01 mol) in MeOH (50 mL) was added Raney Ni (0.23 g, 10%) under N2 protection. The mixture was stirred under hydrogen atmosphere (1 atm) at 30° C. for 1 h. The catalyst was filtered off and the filtrate was concentrated to dryness under vacuum. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 1:2) to give 2-tert-butyl-1H-pyrrolo[2,3-b]pyridin-5-amine (1.4 g, 70%). 1H-NMR (MeOD, 400 MHz) δ 7.71 (s, 1H), 7.27 (s, 1H), 5.99 (s, 1H), 1.37 (s, 9H). MS (ESI) m/e (M+H+) 190.1.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated to dryness under vacuum
  3. customThe residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 1:2)

Sources & evidence

ORD record
ord-755c81066ec54200be1f6ab24524f621
Source dataset
uspto-grants-2013_10
Patent number
US08563573B2

Reaction notes

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