diethyl 1-(3-azido-2,2-difluoropropyl)-1H-indole-2,6-dicarboxylate → diethyl 1-(3-amino-2,2-difluoropropyl)-1H-indole-2,6-dicarboxylate

HRID 1748293Notes

Reaction equation

HRID 1748293 reaction equation
[N:1]([CH2:4][C:5]([F:27])([F:26])[CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:14]=2)[CH:9]=[C:8]1[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N+]=[N-]>CO.C(Cl)Cl.[Pd]>[NH2:1][CH2:4][C:5]([F:27])([F:26])[CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:14]=2)[CH:9]=[C:8]1[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

4

Reactant 1

HCID 86682394diethyl 1-(3-azido-2,2-difluoropropyl)-1H-indole-2,6-dicarboxylate

Product 1

HCID 67235788diethyl 1-(3-amino-2,2-difluoropropyl)-1H-indole-2,6-dicarboxylateYield 83.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of diethyl 1-(3-azido-2,2-difluoropropyl)-1H-indole-2,6-dicarboxylate (2.5 g, 7.8 mmol) in methanol:CH2Cl2 (1:1, 60 mL) is added 10% palladium on carbon (1.4 g, 1.3 mmol). The reaction mixture is stirred for 3.5 h under H2 atmosphere. The reaction mixture is filtered and the filtrate is concentrated to afford the title crude compound (2.3 g) which is used in the next step without purification.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-df156dcbc4894023b57d5699c8a7c70f
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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