Tetrahydrofuran → 2-{8-[4-fluoro-3-(trifluoromethyl)phenoxy]-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]pyridin-8-yl}propan-2-ol

HRID 71084Notes

Reaction equation

HRID 71084 reaction equation
[F:1][C:2]1[CH:36]=[CH:35][C:5]([O:6][C:7]2(C(OCC)=O)[CH2:12][CH2:11][CH2:10][N:9]3[C:13]([C:16]4[CH:21]=[CH:20][C:19]([N:22]5[CH:26]=[C:25]([CH3:27])[N:24]=[CH:23]5)=[C:18]([O:28][CH3:29])[N:17]=4)=[N:14][N:15]=[C:8]23)=[CH:4][C:3]=1[C:37]([F:40])([F:39])[F:38].[CH3:41][Mg]Br.[Cl-].[NH4+].[CH2:46]1[CH2:50][O:49]CC1>>[F:1][C:2]1[CH:36]=[CH:35][C:5]([O:6][C:7]2([C:50]([OH:49])([CH3:46])[CH3:41])[CH2:12][CH2:11][CH2:10][N:9]3[C:13]([C:16]4[CH:21]=[CH:20][C:19]([N:22]5[CH:26]=[C:25]([CH3:27])[N:24]=[CH:23]5)=[C:18]([O:28][CH3:29])[N:17]=4)=[N:14][N:15]=[C:8]23)=[CH:4][C:3]=1[C:37]([F:39])([F:40])[F:38]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 66606976ethyl 8-[4-fluoro-3-(trifluoromethyl)phenoxy]-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-carboxylateHCID 178418573HCID 178418573, compound

Product 1

HCID 666039702-{8-[4-fluoro-3-(trifluoromethyl)phenoxy]-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]pyridin-8-yl}propan-2-ol

Procedure

To a mixture of ethyl 8-[4-fluoro-3-(trifluoromethyl)phenoxy]-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 (103.1 mg) in THF (1.8 mL) was added methylmagnesium bromide (1M THF solution, 920 μL) at room temperature, and the mixture was stirred at room temperature 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 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 (31.5 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and 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 (NH, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-02ea80da21e448a1b149dbaf01e53cde
Source dataset
uspto-grants-2014_09
Patent number
US08822699B2

Reaction notes

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