Methanol → HCID 70313621, compound

HRID 1918201Notes

Reaction equation

HRID 1918201 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:28]=[C:13]3[CH:14]=[C:15]([C:18]4[C:19]([F:27])=[C:20]([C:23]([F:26])=[CH:24][CH:25]=4)[CH:21]=[O:22])[CH:16]=[CH:17][N:12]3[N:11]=2)=[CH:6][CH:5]=1.CO.[Cl-].[NH4+]>ClCCl.O.O1CCCC1>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:28]=[C:13]3[CH:14]=[C:15]([C:18]4[C:19]([F:27])=[C:20]([CH2:21][OH:22])[C:23]([F:26])=[CH:24][CH:25]=4)[CH:16]=[CH:17][N:12]3[N:11]=2)=[CH:8][CH:9]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 86675963HCID 86675963, compound

Product 1

HCID 70313621HCID 70313621, compoundYield 48%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.040 g (1.06 mmol) of sodium borohydride is added portionwise to a solution, cooled to approximately 5° C., of 0.135 g (0.37 mmol) of 3-[2-(4-chlorophenyl)pyrazolo[1,5-a]pyridin-5-yl]-2,6-difluorobenzaldehyde in 10 ml of a mixture of methanol and tetrahydrofuran (1/1). The medium is stirred at ambient temperature for 1 hour, then cooled to 5° C. and then hydrolysed by dropwise addition of 10 ml of a saturated aqueous ammonium chloride solution and 10 ml of water. The mixture is concentrated under reduced pressure and the residue obtained is taken up in 50 ml of dichloromethane and 50 ml of water. The medium is subsequently 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 1 g of silica. The residue is purified by chromatography on silica gel, elution being carried out with a mixture of cyclohexane and ethyl acetate (8/2). 0.065 g (48%) of the expected product is obtained in the form of a white powder.

Workup

  1. temperaturecooled to 5° C.
  2. concentrationThe mixture is concentrated under reduced pressure
  3. customthe residue obtained
  4. filtrationThe medium is subsequently filtered through a hydrophobic cartridge (70 ml liquid/liquid extraction column, Radleys®)
  5. customthe organic phase is recovered
  6. concentrationconcentrated under reduced pressure
  7. additionafter having added 1 g of silica
  8. customThe residue is purified by chromatography on silica gel, elution
  9. additionbeing carried out with a mixture of cyclohexane and ethyl acetate (8/2)

Sources & evidence

ORD record
ord-2d585e71fb6546619286f95f7338e94d
Source dataset
uspto-grants-2013_12
Patent number
US08618301B2

Reaction notes

Loading…