Potassium Carbonate → ethyl 8-(3,4-difluorophenoxy)-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate

HRID 1398214Notes

Reaction equation

HRID 1398214 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].C(=O)([O-])[O-].[K+].[K+].Cl[C:17]1([C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH2:22][CH2:21][CH2:20][N:19]2[C:23]([C:26]3[CH:31]=[CH:30][C:29]([N:32]4[CH:36]=[C:35]([CH3:37])[N:34]=[CH:33]4)=[C:28]([O:38][CH3:39])[N:27]=3)=[N:24][N:25]=[C:18]12>CN(C=O)C.C(OCC)(=O)C.[Cl-].[NH4+]>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[F:8])[O:9][C:17]1([C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH2:22][CH2:21][CH2:20][N:19]2[C:23]([C:26]3[CH:31]=[CH:30][C:29]([N:32]4[CH:36]=[C:35]([CH3:37])[N:34]=[CH:33]4)=[C:28]([O:38][CH3:39])[N:27]=3)=[N:24][N:25]=[C:18]12

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 759273,4-DifluorophenolHCID 66607848ethyl 8-chloro-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate

Product 1

HCID 66608451ethyl 8-(3,4-difluorophenoxy)-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylateYield 49.9%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 3,4-difluorophenol (59 mg) and potassium carbonate (0.18 g) in DMF (4 mL) was added ethyl 8-chloro-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate (0.18 g) at room temperature, and the mixture was stirred at 100° C. for 30 min. The reaction mixture was cooled to room temperature, and diluted with ethyl acetate and saturated aqueous ammonium chloride solution, the mixture was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.11 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washthe mixture was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-750d0f02dea0461996a6380a7152dc56
Source dataset
uspto-grants-2014_12
Patent number
US08901309B2

Reaction notes

Loading…