Sodium Hydroxide → (4-chloro-1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)(phenyl)methanone

HRID 563445Notes

Reaction equation

HRID 563445 reaction equation
O[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.P(Cl)(Cl)([Cl:27])=O.[OH-].[Na+]>>[Cl:27][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

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 178519487(4-hydroxy-1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)(phenyl)methanone

Product 1

HCID 67005674(4-chloro-1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)(phenyl)methanoneYield 66%

Conditions

Temperature
110 °C

Procedure

A mixture of (4-hydroxy-1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)(phenyl)methanone (0.38 g, 1.2 mmol) and phosphorus oxychloride (1.3 mL) was stirred at 110° C. for 1.5 hr. The mixture was cooled, poured onto ice, basified with sodium hydroxide aqueous solution to pH=8, and extracted with ethyl acetate. Combined extracts were dried (Na2SO4) and concentrated. Flash chromatography gave (4-chloro-1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)(phenyl)methanone (0.26 g, 0.79 mmol, 66% yield) as a yellow solid.

Workup

  1. temperatureThe mixture was cooled
  2. additionpoured onto ice
  3. extractionextracted with ethyl acetate
  4. dry with materialCombined extracts were dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f6b593067ed9489c833c3de3077bfe3c
Source dataset
uspto-grants-2011_11
Patent number
US08067447B2

Reaction notes

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