Sodium Carbonate → HCID 51029735, compound

HRID 1918199Notes

Reaction equation

HRID 1918199 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.[CH3:25][Mg]Br.[Cl-].[NH4+].C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.O.ClCCl>[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])[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

8

Reactant 4

HCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 86675962HCID 86675962, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 51029735HCID 51029735, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.072 g (0.23 mmol) of 3-[2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-5-yl]benzaldehyde are dissolved in 10 ml of tetrahydrofuran under a stream of nitrogen. The medium is cooled to 0° C. for slow addition of 0.23 ml (0.68 mmol) of a methylmagnesium bromide solution (3M in ethyl ether). The medium is subsequently brought back to ambient temperature and stirred for 1 hour 30 minutes. Neutralization is carried out by adding, under cold conditions and dropwise, a saturated aqueous ammonium chloride solution and then dilution is carried out with dichloromethane and water. The pH of the medium is adjusted to 9-10 by addition of a saturated aqueous sodium carbonate solution. The medium is filtered through a hydrophobic cartridge (70 ml liquid/liquid extraction column, Radleys®) and the organic phase is recovered and concentrated under reduced pressure after having added 0.8 g of silica. The residue obtained is purified by chromatography on silica gel, elution of the solid deposit being carried out with a mixture of cyclohexane and ethyl acetate (8/2). 0.056 g (74%) of the expected product is obtained in the form of a white powder.

Workup

  1. customis subsequently brought back to ambient temperature
  2. additionby adding, under cold conditions
  3. filtrationThe medium is filtered through a hydrophobic cartridge (70 ml liquid/liquid extraction column, Radleys®)
  4. customthe organic phase is recovered
  5. concentrationconcentrated under reduced pressure
  6. additionafter having added 0.8 g of silica
  7. customThe residue obtained
  8. customis purified by chromatography on silica gel, elution of the solid deposit
  9. additionbeing carried out with a mixture of cyclohexane and ethyl acetate (8/2)

Sources & evidence

ORD record
ord-da889b3ae3304da7abb65006ea36157d
Source dataset
uspto-grants-2013_12
Patent number
US08618301B2

Reaction notes

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