2,6-Difluoro-3-[2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-5-yl]benzaldehyde → 1-{2,6-Difluoro-3-[2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-5-yl]phenyl}prop-2-yn-1-ol

HRID 1036650Notes

Reaction equation

HRID 1036650 reaction equation
[F:1][C:2]1[C:9]([C:10]2[CH:15]=[CH:14][N:13]3[N:16]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)[CH:18]=[C:12]3[CH:11]=2)=[CH:8][CH:7]=[C:6]([F:26])[C:3]=1[CH:4]=[O:5].[C:27]([Mg]Br)#[CH:28]>O1CCCC1>[F:1][C:2]1[C:9]([C:10]2[CH:15]=[CH:14][N:13]3[N:16]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)[CH:18]=[C:12]3[CH:11]=2)=[CH:8][CH:7]=[C:6]([F:26])[C:3]=1[CH:4]([OH:5])[C:27]#[CH:28]

Participants

4

Reactant 2

HCID 866728612,6-Difluoro-3-[2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-5-yl]benzaldehydeHCID 178418486HCID 178418486, compound

Product 1

HCID 866728621-{2,6-Difluoro-3-[2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-5-yl]phenyl}prop-2-yn-1-olYield 58.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The procedure described in stage 2.5 is followed, starting with 0.270 g (0.77 mmol) of 2,6-difluoro-3-[2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-5-yl]benzaldehyde obtained in stage 6.1, in solution in 15 ml of tetrahydrofuran, followed by addition of 4.60 ml (2.30 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 (1/3), 0.171 g (57%) of the expected product is obtained in the form of a pale yellow powder.

Workup

  1. washafter chromatography on silica gel, elution
  2. additionbeing carried out with a mixture of cyclohexane and dichloromethane (1/3)

Sources & evidence

ORD record
ord-0f1c444a1add4611b6d5ca0caad8b495
Source dataset
uspto-grants-2013_10
Patent number
US08546424B2

Reaction notes

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