Ammonium Chloride → (4-chloro-1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)(phenyl)methanol

HRID 563446Notes

Reaction equation

HRID 563446 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])=[CH:6][N:5]=[C:4]2[N:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:17]=[CH:18][C:3]=12.[BH4-].[Na+].[Cl-].[NH4+]>C1COCC1.C(O)C>[Cl:1][C:2]1[C:7]([CH:8]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[OH:9])=[CH:6][N:5]=[C:4]2[N:16]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:17]=[CH:18][C:3]=12

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 67005674(4-chloro-1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)(phenyl)methanone

Product 1

HCID 67005656(4-chloro-1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)(phenyl)methanolYield 100%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (4-chloro-1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)(phenyl)methanone (0.16 g, 0.48 mmol) in THF (1.5 mL) and ethanol (95%, 1.5 mL) was added sodium borohydride (30 mg, 0.79 mmol). The mixture was stirred at rt for 30 min before saturated ammonium chloride aqueous solution was added with caution. The mixture was concentrated and partitioned between water and ethyl acetate. The aqueous layer was separated and extracted with ethyl acetate. Combined organic solutions were dried (Na2SO4), filtered through a pad of silica gel, and concentrated to give (4-chloro-1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)(phenyl)methanol (0.16 g, 0.48 mmol, 100% yield) as a yellow solid.

Workup

  1. additionwas added with caution
  2. concentrationThe mixture was concentrated
  3. custompartitioned between water and ethyl acetate
  4. customThe aqueous layer was separated
  5. extractionextracted with ethyl acetate
  6. dry with materialCombined organic solutions were dried (Na2SO4)
  7. filtrationfiltered through a pad of silica gel
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-979c3bbda09b427480a28f621d3b0144
Source dataset
uspto-grants-2011_11
Patent number
US08067447B2

Reaction notes

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