Ammonium formate → 1-tert-butyl 2-ethyl 4-hydroxy-1H-indole-1,2-dicarboxylate

HRID 1929079Notes

Reaction equation

HRID 1929079 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:7]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:8]2[C:13]([CH:14]=1)=[C:12]([O:15]CC1C=CC=CC=1)[CH:11]=[CH:10][CH:9]=2)=[O:5].C([O-])=O.[NH4+]>C(O)C.[Pd]>[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:7]([C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])[C:8]2[C:13]([CH:14]=1)=[C:12]([OH:15])[CH:11]=[CH:10][CH:9]=2)=[O:5]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 591526751-tert-butyl 2-ethyl 4-(benzyloxy)-1H-indole-1,2-dicarboxylate

Product 1

HCID 596001381-tert-butyl 2-ethyl 4-hydroxy-1H-indole-1,2-dicarboxylateYield 19.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

103 (46.2 g, 116.8 mmol) is dissolved in ethanol (300 ml) and after addition of ammonium formiate (8.3 g, 128.5 mmol) and 10% Pd—C (5 g) the mixture is stirred at room temperature for 1 h. Then the mixture is filtered off. Evaporation under reduced pressure gave 6.89 g of a white solid, which is further purified by recrystallisation from ether/hexanes.

Workup

  1. filtrationThen the mixture is filtered off
  2. customEvaporation under reduced pressure

Sources & evidence

ORD record
ord-3ab3a5a2f2504df4b076b2798ab06f28
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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