Methanol → HCID 70312810, compound

HRID 1918202Notes

Reaction equation

HRID 1918202 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[CH:26]=[C:25]5[C:21]([CH2:22][CH2:23][C:24]5=[O:27])=[CH:20][CH:19]=4)[CH:16]=[CH:17][N:12]3[N:11]=2)=[CH:6][CH:5]=1.CO.[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C.O>[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[CH:26]=[C:25]5[C:21]([CH2:22][CH2:23][CH:24]5[OH:27])=[CH:20][CH:19]=4)[CH:16]=[CH:17][N:12]3[N:11]=2)=[CH:6][CH:5]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 70312758HCID 70312758, compound

Product 1

HCID 70312810HCID 70312810, compoundYield 67.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

0.040 g (1.06 mmol) of sodium borohydride is added portionwise to a solution, cooled to approximately 5° C., of 0.12 g (0.33 mmol) of 6-[2-(4-chlorophenyl)pyrazolo[1,5-a]pyridin-5-yl]indanone in 16 ml of a 1/1 mixture of methanol and tetrahydrofuran. The medium is stirred at 70° C. for 2 hours, then cooled to 0° C. and then hydrolysed by dropwise addition of 10 ml of a saturated aqueous ammonium chloride solution. The medium is subsequently diluted with 50 ml of ethyl acetate and 30 ml of water. The organic phase is recovered and the aqueous phase is extracted with 30 ml of ethyl acetate. The organic phases are combined, dried over sodium sulphate and then concentrated under reduced pressure. The residue obtained by solid deposition is purified by chromatography on silica gel, elution being carried out with a mixture of cyclohexane and ethyl acetate (8/2). 0.080 g (66%) of the expected product is obtained in the form of a white powder.

Workup

  1. temperaturecooled to 0° C.
  2. customThe organic phase is recovered
  3. extractionthe aqueous phase is extracted with 30 ml of ethyl acetate
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained by solid deposition
  7. customis purified by chromatography on silica gel, elution
  8. additionbeing carried out with a mixture of cyclohexane and ethyl acetate (8/2)

Sources & evidence

ORD record
ord-7a69eb568f944e26871de6b1721eb719
Source dataset
uspto-grants-2013_12
Patent number
US08618301B2

Reaction notes

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