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

HRID 2250326Notes

Reaction equation

HRID 2250326 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 2 C) 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. The mixture is then poured into 1 l of water and extracted three times with 0.5 l 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 0.5 l 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-248c2c470700421d99044f46d5cca63b
Source dataset
uspto-grants-2008_01
Patent number
US07317016B2

Reaction notes

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