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

HRID 1804759Notes

Reaction equation

HRID 1804759 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+]>[Pd].C(O)C>[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-dicarboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

10% Palladium on carbon (1 g) is placed under an argon atmosphere into a round-bottom flask and covered with 50 ml of ethanol. A solution of (4-benzyloxy-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (1) (35 g, 88.5 mmol) in 250 ml ethanol is added, followed by ammonium formiate (6.3 g, 97.4 mmol). The mixture is stirred for 30 min at rt (TLC control). After completion of the reaction, the mixture is filtrated and evaporation gives a white solid, which is further purified by recrystallization from diethyl ether/hexanes.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe mixture is filtrated
  3. customevaporation
  4. customgives a white solid, which
  5. customis further purified by recrystallization from diethyl ether/hexanes

Sources & evidence

ORD record
ord-2d813ae1348546d59a8b455ab7c99091
Source dataset
uspto-grants-2013_01
Patent number
US08354431B2

Reaction notes

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