HCID 86672865, compound → HCID 86672866, compound

HRID 1036655Notes

Reaction equation

HRID 1036655 reaction equation
[C:1]1([CH3:24])[CH:6]=[CH:5][C:4]([C:7]2[CH:23]=[C:10]3[CH:11]=[C:12]([C:15]4[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=4)[CH:18]=[O:19])[CH:13]=[CH:14][N:9]3[N:8]=2)=[CH:3][CH:2]=1.[C:25]([Mg]Br)#[CH:26]>O1CCCC1>[C:1]1([CH3:24])[CH:2]=[CH:3][C:4]([C:7]2[CH:23]=[C:10]3[CH:11]=[C:12]([C:15]4[CH:16]=[C:17]([CH:18]([OH:19])[C:25]#[CH:26])[CH:20]=[CH:21][CH:22]=4)[CH:13]=[CH:14][N:9]3[N:8]=2)=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 86672865HCID 86672865, compoundHCID 178418486HCID 178418486, compound

Product 1

HCID 86672866HCID 86672866, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The procedure described in stage 2.5 is followed, starting with 0.105 g (0.34 mmol) of 3-(2-{p-tolyl}pyrazolo[1,5-a]pyridin-5-yl)benzaldehyde obtained in stage 8.4, in solution in 15 ml of tetrahydrofuran, followed by addition of 3.20 ml (1.60 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 ethyl acetate (8/2), 0.062 g (54%) of the expected product is obtained in the form of a yellow powder.

Workup

  1. washafter chromatography on silica gel, elution
  2. additionbeing carried out with a mixture of cyclohexane and ethyl acetate (8/2)

Sources & evidence

ORD record
ord-f696b2d7898143f6a3ee98e09cb4d8d5
Source dataset
uspto-grants-2013_10
Patent number
US08546424B2

Reaction notes

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