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

HRID 1398197

Reaction equation

HRID 1398197 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[F:5][C:6]1[CH:7]=[C:8]([CH:38]=[CH:39][C:40]=1[F:41])[O:9][C:10]1([C:33](OCC)=[O:34])[CH2:15][CH2:14][CH2:13][N:12]2[C:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]4[O:29][C:28]([CH3:30])=[N:27][CH:26]=4)=[C:21]([O:31][CH3:32])[CH:20]=3)=[N:17][N:18]=[C:11]12.[Cl-].[NH4+].[CH2:44]1COC[CH2:45]1>>[F:5][C:6]1[CH:7]=[C:8]([CH:38]=[CH:39][C:40]=1[F:41])[O:9][C:10]1([C:33]([OH:34])([CH2:1][CH3:2])[CH2:44][CH3:45])[CH2:15][CH2:14][CH2:13][N:12]2[C:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]4[O:29][C:28]([CH3:30])=[N:27][CH:26]=4)=[C:21]([O:31][CH3:32])[CH:20]=3)=[N:17][N:18]=[C:11]12

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 66609151Ethyl 8-(3,4-difluorophenoxy)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylateHCID 178418443HCID 178418443, compound

Product 1

HCID 666039593-{8-(3,4-Difluorophenoxy)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-8-yl}pentan-3-ol

Procedure

Under an argon atmosphere, ethylmagnesium bromide (1M THF solution, 11.8 mL) was added to a suspension of ethyl 8-(3,4-difluorophenoxy)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate (1200 mg) in THF (12 mL) under ice-cooling. The reaction mixture was stirred under ice-cooling for 1 hr, saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate) to give the title compound (230 mg).

Workup

  1. temperaturecooling
  2. temperaturecooling for 1 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate)

Sources & evidence

ORD record
ord-d38a847e17174c018874ca8a652d1273
Source dataset
uspto-grants-2014_12
Patent number
US08901309B2

Linked notes

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