Ammonium formate → HCID 63758165, compound

HRID 1521750Notes

Reaction equation

HRID 1521750 reaction equation
C([O-])=O.[NH4+].Cl[C:6]1[N:11]=[C:10]2[N:12]([CH2:16][CH3:17])[C:13]([NH2:15])=[N:14][C:9]2=[CH:8][CH:7]=1>C(O)C.[Pd]>[CH2:16]([N:12]1[C:10]2=[N:11][CH:6]=[CH:7][CH:8]=[C:9]2[N:14]=[C:13]1[NH2:15])[CH3:17]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 86682396HCID 86682396, compound

Product 1

HCID 63758165HCID 63758165, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ammonium formate (1.55 g, 24.6 mmol) is added to a solution of 5-chloro-3-ethyl-3H-imidazo[4,5-b]pyridin-2-amine (410 mg, 2.09 mmol) in ethanol (10 mL) containing 10% palladium on carbon (40 mg). The mixture is stirred at room temperature for 16 h. The reaction is filtered, concentrated under reduced pressure and the residue is purified via flash column chromatography using a gradient elution of 0-10% CH2Cl2/methanol to afford the title compound (192 mg, 57%).

Workup

  1. filtrationThe reaction is filtered
  2. concentrationconcentrated under reduced pressure
  3. customthe residue is purified via flash column chromatography
  4. washa gradient elution of 0-10% CH2Cl2/methanol

Sources & evidence

ORD record
ord-69565b8695ff41d99d7d4a83e4316466
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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