Sodium Bicarbonate → 2,2,2-Trifluoro-1-(1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)ethanol

HRID 244396Notes

Reaction equation

HRID 244396 reaction equation
Cl[C:2]1[C:7]([C:8]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)([OH:13])[C:9]([F:12])([F:11])[F:10])=[CH:6][N:5]=[C:4]2[N:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:24]=[CH:25][C:3]=12.C(=O)(O)[O-].[Na+]>C(O)(=O)C.[Zn]>[F:12][C:9]([F:10])([F:11])[C:8]([C:7]1[CH:2]=[C:3]2[CH:25]=[N:24][N:23]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:4]2=[N:5][CH:6]=1)([C:14]1[C:22]2[C:17](=[N:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)[OH:13]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 249587271-(4-Chloro-1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)-2,2,2-trifluoro-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)ethanol

Product 1

HCID 249587262,2,2-Trifluoro-1-(1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)ethanolYield 78.7%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 200 mg (0.45 mmol) of 1-(4-chloro-1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)-2,2,2-trifluoro-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)ethanol and 185 mg (2.83 mmol) of zinc powder in acetic acid was warmed at reflux for 30 minutes. The mixture was then cooled and made basic with saturated aqueous sodium bicarbonate and extracted with three 30 mL portions of ethyl acetate. The combined organic layers were washed with two 15 mL portions of saturated aqueous sodium bicarbonate, three 15 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 145 mg (78%) of the title compound. The material from the column was triturated with ether-hexanes to afford 85 mg of the title compound as a white solid. The solid was dried under house vacuum at 90° C. and then 110° C. MS m/z 410.30 (MH+), m.p. 137° C.-141° C.

Workup

  1. temperaturewas warmed
  2. temperatureat reflux for 30 minutes
  3. temperatureThe mixture was then cooled
  4. extractionextracted with three 30 mL portions of ethyl acetate
  5. washThe combined organic layers were washed with two 15 mL portions of saturated aqueous sodium bicarbonate, three 15 mL portions of brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-639fc5d13eec48a49a6bc3196bbed232
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Reaction notes

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