Ammonium formate → Ethyl 5-amino-1-(2-fluorobenzyl)-1H-indole-2-carboxylate

HRID 1824982Notes

Reaction equation

HRID 1824982 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([N+:14]([O-])=O)=[CH:11][CH:12]=2)[CH:7]=[C:6]1[C:17]([O:19][CH2:20][CH3:21])=[O:18].C([O-])=O.[NH4+]>C(OCC)(=O)C.C(O)C.[Pd]>[NH2:14][C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[N:5]([CH2:4][C:3]1[CH:22]=[CH:23][CH:24]=[CH:25][C:2]=1[F:1])[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:7]2

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 12068605Ethyl 1-(2-fluorobenzyl)-5-nitro-1H-indole-2-carboxylate

Product 1

HCID 22144678Ethyl 5-amino-1-(2-fluorobenzyl)-1H-indole-2-carboxylate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

27.84 g (81.33 mmol) of ethyl 1-(2-fluorobenzyl)-5-nitro-1H-indole-2-carboxylate from Example II are initially charged in 750 ml of ethyl acetate and 750 ml of ethanol. 20.51 g (325.31 mmol) of ammonium formate and 2.78 g of palladium on activated carbon are added. The mixture is boiled at reflux and, after one hour, cooled and filtered off through kieselguhr. The filter cake is washed with ethyl acetate. The solvent is removed under reduced pressure and the residue is dried.

Workup

  1. temperatureat reflux and, after one hour
  2. temperaturecooled
  3. filtrationfiltered off through kieselguhr
  4. washThe filter cake is washed with ethyl acetate
  5. customThe solvent is removed under reduced pressure
  6. customthe residue is dried

Sources & evidence

ORD record
ord-2e7dc7ae76a34a628e15872cc7987b06
Source dataset
uspto-grants-2006_05
Patent number
US07045544B2

Reaction notes

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