4-[(4-nitro-1H-indol-1-yl)methyl]-1-(t-butyloxycarbonyl)-1H-pyrrolo[2,3-b]pyridine → 4-[(4-amino-1H-indol-1-yl)methyl]-1-(t-butyloxycarbonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 240474Notes

Reaction equation

HRID 240474 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[CH2:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]2[N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:21]=[CH:22][C:15]=12)([O-])=O>[Pd].C1COCC1>[NH2:1][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[CH2:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]2[N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:21]=[CH:22][C:15]=12

Participants

4

Reactant 1

HCID 687484114-[(4-nitro-1H-indol-1-yl)methyl]-1-(t-butyloxycarbonyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 687490074-[(4-amino-1H-indol-1-yl)methyl]-1-(t-butyloxycarbonyl)-1H-pyrrolo[2,3-b]pyridineYield 95.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a round-bottom flask was added 4-[(4-nitro-1H-indol-1-yl)methyl]-1-(t-butyloxycarbonyl)-1H-pyrrolo[2,3-b]pyridine (500 mg, 1.3 mmol), Palladium on carbon (50 mg, 10%), and THF (30 mL). The mixture was stirred under a hydrogen atmosphere for 2 h, then filtered, concentrated to afford 4-[(4-amino-1H-indol-1-yl)methyl]-1-(t-butyloxycarbonyl)-1H-pyrrolo[2,3-b]pyridine (450 mg).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-acc086089f984604bbb8543e8607f3a4
Source dataset
uspto-grants-2014_02
Patent number
US08648086B2

Reaction notes

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