Ammonium formate → 2-(cis-3-Methoxy-cyclohexyloxy)-pyridin-3-ylamine

HRID 406042Notes

Reaction equation

HRID 406042 reaction equation
C([O-])=O.[NH4+].[CH3:5][O:6][C@@H:7]1[CH2:12][CH2:11][CH2:10][C@H:9]([O:13][C:14]2[C:19]([N+:20]([O-])=O)=[CH:18][CH:17]=[CH:16][N:15]=2)[CH2:8]1>[Pd].CO.ClCCl.O>[CH3:5][O:6][C@@H:7]1[CH2:12][CH2:11][CH2:10][C@H:9]([O:13][C:14]2[C:19]([NH2:20])=[CH:18][CH:17]=[CH:16][N:15]=2)[CH2:8]1

Participants

7

Reactant 2

HCID 2723923Ammonium formateHCID 673825062-(cis-3-Methoxy-cyclohexyloxy)-3-nitro-pyridine

Product 1

HCID 673821972-(cis-3-Methoxy-cyclohexyloxy)-pyridin-3-ylamine

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Ammonium formate (7.25 g) was added to a suspension of 2-(cis-3-methoxy-cyclohexyloxy)-3-nitro-pyridine (5.80 g) and 10% palladium on charcoal (400 mg) in methanol (40 ml) at room temperature and the mixture was heated to reflux for 30 min until LCMS indicated complete conversion of the starting material. The mixture was diluted with dichloromethane (100 ml) and water (40 ml), filtered through celite, and the filtercake was washed with dichloromethane (30 ml). The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was submitted to column chromatography (silica gel, petrol ether/ethyl acetate 70:30) to give the desired product.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 30 min until LCMS
  3. filtrationfiltered through celite
  4. washthe filtercake was washed with dichloromethane (30 ml)
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-140377cf0a6d497e8153c8a12ccd715d
Source dataset
uspto-grants-2014_06
Patent number
US08754079B2

Reaction notes

Loading…