Ammonium formate → HCID 63758165, compound

HRID 1748323Notes

Reaction equation

HRID 1748323 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 for 16 h, filtered, and concentrated. The residue is purified via flash column chromatography using a gradient of 0-10% methanol in CH2Cl2 to afford the title compound (192 mg, 57%).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe residue is purified via flash column chromatography

Sources & evidence

ORD record
ord-45c45dda6501426482f5b8aa84cdfb58
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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