Water → 4-{4-Chloro-3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-1-yl}-3-methylbenzonitrile

HRID 921574Notes

Reaction equation

HRID 921574 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N:10]1[C:14]2[NH:15][CH:16]=[CH:17][C:18](=O)[C:13]=2[C:12]([C:20]([F:23])([F:22])[F:21])=[N:11]1)[C:5]#[N:6].S(Cl)([Cl:26])=O.CN(C=O)C.O>C(Cl)(Cl)Cl>[Cl:26][C:18]1[CH:17]=[CH:16][N:15]=[C:14]2[N:10]([C:9]3[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=3[CH3:1])[N:11]=[C:12]([C:20]([F:23])([F:22])[F:21])[C:13]=12

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 1363901483-Methyl-4-{4-oxo-3-(trifluoromethyl)-4,7-dihydro-1H-pyrazolo[3,4-b]pyridin-1-yl}benzonitrile

Product 1

HCID 675025754-{4-Chloro-3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-1-yl}-3-methylbenzonitrileYield 71%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Compound (154d) (2.20 g) was dissolved in chloroform (14 mL), and thionyl chloride (1.00 mL) and DMF (0.148 mL) were added to the resulting solution, followed by reflux for 3 hr. Water was added to the reaction solution for distribution. The organic layer was washed with saturated sodium bicarbonate water. The organic layer after the washing was dried over anhydrous sodium sulfate, and the solvent was distilled away. 2-Propanol was added to the residue, and the precipitate was collected by filtration and then dried under reduced pressure to obtain compound (154e) (1.60 g, 71%).

Workup

  1. temperatureby reflux for 3 hr
  2. washThe organic layer was washed with saturated sodium bicarbonate water
  3. dry with materialThe organic layer after the washing was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled away
  5. addition2-Propanol was added to the residue
  6. filtrationthe precipitate was collected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-e06140f750914345b86c48101c6137f7
Source dataset
uspto-grants-2016_03
Patent number
US09273045B2

Reaction notes

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