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

HRID 2120568Notes

Reaction equation

HRID 2120568 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 3C) are dissolved in 330 ml of THF and treated with 27 g (341 mmol) of pyridine. 47.76 ml (71.66 g, 341 mmol) of trifluoroacetic anhydride are then added in the course of 10 min, the temperature rising to 40° C. The mixture is stirred overnight at room temperature. The batch is then added to 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 hydrogencarbonate solution and with 1 N HCl dried using MgSO4 and concentrated in a rotary evaporator.

Workup

  1. customrising 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 hydrogencarbonate solution and with 1 N HCl
  4. customdried
  5. concentrationconcentrated in a rotary evaporator

Sources & evidence

ORD record
ord-280a6bc05c0e4cf08b81c2c285d7a7c1
Source dataset
uspto-grants-2004_02
Patent number
US06693102B2

Reaction notes

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