Iodoethane → 2-{8-(3,4-Difluorophenoxy)-3-[3-ethoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-8-yl}propan-2-ol

HRID 1398228Notes

Reaction equation

HRID 1398228 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][C:34]=1[F:35])[O:5][C:6]1([C:28]([OH:31])([CH3:30])[CH3:29])[CH2:11][CH2:10][CH2:9][N:8]2[C:12]([C:15]3[CH:16]=[CH:17][C:18]([C:22]4[O:26][C:25]([CH3:27])=[N:24][CH:23]=4)=[C:19]([OH:21])[CH:20]=3)=[N:13][N:14]=[C:7]12.C(=O)([O-])[O-].[K+].[K+].I[CH2:43][CH3:44].C(OCC)(=O)C>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][C:34]=1[F:35])[O:5][C:6]1([C:28]([OH:31])([CH3:30])[CH3:29])[CH2:11][CH2:10][CH2:9][N:8]2[C:12]([C:15]3[CH:16]=[CH:17][C:18]([C:22]4[O:26][C:25]([CH3:27])=[N:24][CH:23]=4)=[C:19]([O:21][CH2:43][CH3:44])[CH:20]=3)=[N:13][N:14]=[C:7]12

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 66604162HCID 66604162, compound

Product 1

HCID 666042882-{8-(3,4-Difluorophenoxy)-3-[3-ethoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-8-yl}propan-2-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-[8-(3,4-difluorophenoxy)-8-(1-hydroxy-1-methylethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-3-yl]-2-(2-methyl-1,3-oxazol-5-yl)phenol (41.1 mg) and potassium carbonate (24 mg) in DMF (0.43 ml) was added iodoethane (60 μL) at room temperature, and the mixture was stirred overnight. To the reaction mixture was added ethyl acetate, 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 (NH, ethyl acetate/hexane) to give the title compound (38.1 mg).

Workup

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

Sources & evidence

ORD record
ord-6057abceac2649998e630f4235fbec94
Source dataset
uspto-grants-2014_12
Patent number
US08901309B2

Reaction notes

Loading…