Ammonium formate → HCID 57901694, compound

HRID 1851383Notes

Reaction equation

HRID 1851383 reaction equation
C([NH:8][C:9]1[N:10]=[CH:11][CH:12]=[C:13]2[CH:17]=[C:16]([C:18]([O:20][CH3:21])=[O:19])[NH:15][C:14]=12)C1C=CC=CC=1.C([O-])=O.[NH4+]>[C].[Pd].CO>[NH2:8][C:9]1[N:10]=[CH:11][CH:12]=[C:13]2[CH:17]=[C:16]([C:18]([O:20][CH3:21])=[O:19])[NH:15][C:14]=12

Participants

5

Reactant 2

HCID 2723923Ammonium formate2×HCID 57901817HCID 57901817, compound

Product 1

HCID 57901694HCID 57901694, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl 7-(benzylamino)-1H-pyrrolo[2,3-c]pyridine-2-carboxylate (3.2 g), ammonium formate (7.2 g), 10% palladium-carbon (50% containing water, 3.2 g) and methanol (120 mL) was heated under reflux for 4 hr. Ammonium formate (6.0 g) was further added to the reaction solution, and the mixture was heated under reflux for 16 hr. The insoluble material was filtered off by passing the reaction solution through celite without cooling. The filtrate was concentrated and the obtained crystals were washed with methanol to give the title compound (1.62 g, yield 75%) as pale-yellow prism crystals. melting point not less than 300° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hr
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 16 hr
  5. filtrationThe insoluble material was filtered off
  6. temperaturewithout cooling
  7. concentrationThe filtrate was concentrated
  8. washthe obtained crystals were washed with methanol

Sources & evidence

ORD record
ord-2a1cf1b22a774e62b5d9e9a90d18e870
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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