Ethyl Acetate → HCID 51029730, compound

HRID 1918197Notes

Reaction equation

HRID 1918197 reaction equation
[Cl: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.[CH3:25][Mg]Br.[Cl-].[NH4+].C(OCC)(=O)C>O1CCCC1.O>[Cl: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])[CH3:25])[CH:21]=[CH:22][CH:23]=4)[CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 86675961HCID 86675961, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 51029730HCID 51029730, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.085 g (0.26 mmol) of 3-[2-(4-chlorophenyl)pyrazolo[1,5-a]pyridin-5-yl]benzaldehyde is dissolved in 8 ml of tetrahydrofuran under a stream of nitrogen. The medium is cooled to 5° C. before slow addition of 0.30 ml (0.90 mmol) of a methylmagnesium bromide solution (3M in ethyl ether). The medium is subsequently stirred at ambient temperature for 2 hours. Neutralization is carried out by adding, under cold conditions and dropwise, a saturated aqueous ammonium chloride solution and then dilution is carried out with ethyl acetate and water. The organic phase is separated and then the aqueous phase is extracted twice with ethyl acetate. The organic phases are combined, dried over sodium sulphate, filtered and concentrated under vacuum. The residue is purified by chromatography on silica gel (by solid deposit), elution being carried out with a mixture of cyclohexane and ethyl acetate (8/2). 0.048 g (53%) of the expected product is obtained in the form of a white powder.

Workup

  1. additionby adding, under cold conditions
  2. customThe organic phase is separated
  3. extractionthe aqueous phase is extracted twice with ethyl acetate
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue is purified by chromatography on silica gel (by solid deposit), elution
  8. additionbeing carried out with a mixture of cyclohexane and ethyl acetate (8/2)

Sources & evidence

ORD record
ord-9eae944d99db47579366b9d87409c820
Source dataset
uspto-grants-2013_12
Patent number
US08618301B2

Reaction notes

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