1-{3-[2-(4-Fluorophenyl)pyrazolo[1,5-a]pyridin-5-yl]phenyl}ethanone → 2-{3-[2-(4-Fluorophenyl)pyrazolo[1,5-a]pyridin-5-yl]phenyl}but-3-yn-2-ol

HRID 1036646Notes

Reaction equation

HRID 1036646 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:25]=[C:11]3[CH:12]=[C:13]([C:16]4[CH:17]=[C:18]([C:22](=[O:24])[CH3:23])[CH:19]=[CH:20][CH:21]=4)[CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.[C:26]([Mg]Br)#[CH:27]>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:25]=[C:11]3[CH:12]=[C:13]([C:16]4[CH:17]=[C:18]([C:22]([OH:24])([C:26]#[CH:27])[CH3:23])[CH:19]=[CH:20][CH:21]=4)[CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 703755651-{3-[2-(4-Fluorophenyl)pyrazolo[1,5-a]pyridin-5-yl]phenyl}ethanoneHCID 178418486HCID 178418486, compound

Product 1

HCID 510296392-{3-[2-(4-Fluorophenyl)pyrazolo[1,5-a]pyridin-5-yl]phenyl}but-3-yn-2-olYield 6.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The procedure described in stage 2.5 is followed, starting with 0.261 g (0.79 mmol) of 1-{3-[2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-5-yl]phenyl}ethanone obtained in stage 4.1, in solution in 10 ml of tetrahydrofuran, followed by addition of 4.74 ml (2.37 mmol) of an ethynylmagnesium bromide solution (0.5M in tetrahydrofuran) and after chromatography on silica gel, elution being carried out with a mixture of cyclohexane and dichloromethane (1/9), 0.018 g (6%) of the expected product is obtained in the fowl of a white powder.

Workup

  1. washafter chromatography on silica gel, elution
  2. additionbeing carried out with a mixture of cyclohexane and dichloromethane (1/9)

Sources & evidence

ORD record
ord-da18e4886a7649f3b35e38cc87faa9f5
Source dataset
uspto-grants-2013_10
Patent number
US08546424B2

Reaction notes

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