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Ammonium formate → HCID 22144666, compound

HRID 1824979
Notes
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Reaction equation

HRID 1824979 reaction equation
[F:1][C:2]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][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]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)=[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:27]=[CH:28][C:29]([F:31])=[CH:30][C:2]=1[F:1])[C:6]([C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)=[O:18])=[CH:7]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 2723923Ammonium formate2×HCID 22144644HCID 22144644, compound

Product 1

HCID 22144666HCID 22144666, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolventHCID 8857
Ethyl Acetate
Solvent

Procedure

485 mg (1.14 mmol) of 1-(2,4-difluorobenzyl)-N-(4-fluorophenyl)-5-nitro-1H-indole-2-carboxamide from Example XXIV are initially charged in ethyl acetate and ethanol. 287 mg (4.56 mmol) of ammonium formate and 49 mg of palladium on activated carbon (10%) are added. The mixture is heated to reflux, and at 50° C. gas evolves. To bring the reaction to completion, the same amounts of ammonium formate and palladium as above are added. After a further 3 hours at reflux, the mixture is cooled and filtered off through kieselguhr, which is washed with 500 ml of ethanol. The solvent is removed under reduced pressure and the residue is dried.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux
  3. customat 50° C.
  4. customthe reaction to completion
  5. temperatureAfter a further 3 hours at reflux
  6. temperaturethe mixture is cooled
  7. filtrationfiltered off through kieselguhr, which
  8. washis washed with 500 ml of ethanol
  9. customThe solvent is removed under reduced pressure
  10. customthe residue is dried

Sources & evidence

ORD record
ord-378d339d207348419f28bbc049321e5a
Source dataset
uspto-grants-2006_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07045544B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes