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

HRID 1036648Notes

Reaction equation

HRID 1036648 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:24]=[C:11]3[CH:12]=[C:13]([C:16]4[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=4[CH:18]=[O:19])[CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.[C:25]([Mg]Br)#[CH:26]>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:24]=[C:11]3[CH:12]=[C:13]([C:16]4[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=4[CH:18]([OH:19])[C:25]#[CH:26])[CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 866728602-[2-(4-Fluorophenyl)pyrazolo[1,5-a]pyridin-5-yl]benzaldehydeHCID 178418486HCID 178418486, compound

Product 1

HCID 510296401-{2-[2-(4-Fluorophenyl)pyrazolo[1,5-a]pyridin-5-yl]phenyl}prop-2-yn-1-olYield 30.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The procedure described in stage 2.5 is followed, starting with 0.245 g (0.77 mmol) of 2-[2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-5-yl]benzaldehyde obtained in stage 5.1, in solution in 15 ml of tetrahydrofuran, followed by addition of 4.65 ml (2.32 mmol) of an ethynylmagnesium bromide solution (0.5M in tetrahydrofuran) and after chromatography on silica gel, elution being carried out with dichloromethane, 0.08 g (30%) of the expected product is obtained in the form of a pale yellow powder.

Workup

  1. washafter chromatography on silica gel, elution

Sources & evidence

ORD record
ord-3ad023ed557a4cbab915e4c7e2610579
Source dataset
uspto-grants-2013_10
Patent number
US08546424B2

Reaction notes

Loading…