HCID 86672864, compound → HCID 86672863, compound

HRID 1036652Notes

Reaction equation

HRID 1036652 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:24]=[C:11]2[CH:12]=[C:13]([C:16]3[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=3)[CH:19]=[O:20])[CH:14]=[CH:15][N:10]2[N:9]=1.[C:25]([Mg]Br)#[CH:26]>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:24]=[C:11]2[CH:12]=[C:13]([C:16]3[CH:17]=[C:18]([CH:19]([OH:20])[C:25]#[CH:26])[CH:21]=[CH:22][CH:23]=3)[CH:14]=[CH:15][N:10]2[N:9]=1

Participants

4

Reactant 2

HCID 86672864HCID 86672864, compoundHCID 178418486HCID 178418486, compound

Product 1

HCID 86672863HCID 86672863, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The procedure described in stage 2.5 is followed, starting with 0.125 g (0.40 mmol) of 3-[2-(2-fluorophenyl)pyrazolo[1,5-a]pyridin-5-yl]benzaldehyde obtained in stage 7.2, in solution in 15 ml of tetrahydrofuran, followed by addition of 3.50 ml (1.75 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), 0.112 g (82%) of the expected product is obtained in the fatm of a beige 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-d043289478624fc6a92f54d3e9741fe7
Source dataset
uspto-grants-2013_10
Patent number
US08546424B2

Reaction notes

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