Water → 1-((2-Fluorophenyl)methyl)pyrazolo(3,4-b)pyridine-3-carbonitrile

HRID 1591659Notes

Reaction equation

HRID 1591659 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]([NH2:16])=O)=[N:6]1.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.O>C1COCC1>[C:14]([C:7]1[C:8]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[N:5]([CH2:4][C:3]2[CH:17]=[CH:18][CH:19]=[CH:20][C:2]=2[F:1])[N:6]=1)#[N:16]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 113231781-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboxamide

Product 1

HCID 114025001-((2-Fluorophenyl)methyl)pyrazolo(3,4-b)pyridine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

36.1 g (133 mmol) of 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboxamide from example 2C) are dissolved in 330 ml of THF, and 27 g (341 mmol) of pyridine are added. Then, over the course of 10 min, 47.76 ml (71.66 g, 341 mmol) of trifluoroacetic anhydride are added, during which the temperature rises to 40° C. The mixture is stirred at room temperature overnight. It is then added to 11 of water and extracted three times with 0.51 of ethyl acetate each time. The organic phase is washed with saturated sodium bicarbonate solution and with 1 N HCl, dried with MgSO4 and concentrated in a rotary evaporator.

Workup

  1. customrises to 40° C
  2. extractionextracted three times with 0.51 of ethyl acetate each time
  3. washThe organic phase is washed with saturated sodium bicarbonate solution and with 1 N HCl
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated in a rotary evaporator

Sources & evidence

ORD record
ord-f70a9707908d43c5a6e27665ee73eb0d
Source dataset
uspto-grants-2007_11
Patent number
US07291622B2

Reaction notes

Loading…