t-Butyl 5-nitroindole-2-carboxylate → Tert-butyl 5-amino-1H-indole-2-carboxylate

HRID 2054713Notes

Reaction equation

HRID 2054713 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:7]2)([O-])=O>[Pd].CO.C1COCC1>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:7]2

Participants

4

Reactant 1

HCID 10801431t-Butyl 5-nitroindole-2-carboxylate

Product 1

HCID 10633339Tert-butyl 5-amino-1H-indole-2-carboxylateYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A 500 mL Par hydrogenation bottle was charged with compound 10 (5.80 g, 22.14 mmol), 10% Pd/C (0.6 g) and methanol/THF (150 mL, 1:4 v/v), and purged with hydrogen. The reaction mixture was shaken with 50 psi H2 over night. The catalyst was removed by filtration and the solvent was evaporated to give 4.98 g (97% yield) of the title compound 11 as brown solid. 1H NMR (DMSO), 11.42 (s, 1H), 7.18 (d, 1H, J=8.3 Hz), 6.83 (s, 1H), 6.71 (s, 1H), 6.67 (d, 1H, J=8.4 Hz), 1.62 (s, 9H). This product is unstable and therefore it was immediately used in the following step.

Workup

  1. custompurged with hydrogen
  2. customThe catalyst was removed by filtration
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-dee4c5de01b345eaa9e6d067c60670cd
Source dataset
uspto-grants-2008_02
Patent number
US07329760B2

Reaction notes

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