HCID 86675962, compound → HCID 51029559, compound

HRID 1036644Notes

Reaction equation

HRID 1036644 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:17]=[C:18]([CH:21]=[CH:22][CH:23]=4)[CH:19]=[O:20])[CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.[C:25]([Mg]Br)#[C:26][CH3:27]>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:17]=[C:18]([CH:19]([OH:20])[C:25]#[C:26][CH3:27])[CH:21]=[CH:22][CH:23]=4)[CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 86675962HCID 86675962, compoundHCID 178419101HCID 178419101, compound

Product 1

HCID 51029559HCID 51029559, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The procedure described in stage 2.5 is followed, starting with 0.300 g (0.95 mmol) of 3-[2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-5-yl]benzaldehyde obtained according to the process described in 2.4, in solution in 10 ml of tetrahydrofuran, followed by addition of 5.70 ml (2.85 mmol) of a (propyn-1-yl)magnesium 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), 0.23 g (67%) of the expected product is obtained in the form of a pale yellow powder.

Workup

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

Sources & evidence

ORD record
ord-e481522068274b8f989f00b43d102a2a
Source dataset
uspto-grants-2013_10
Patent number
US08546424B2

Reaction notes

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