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

HRID 346528Notes

Reaction equation

HRID 346528 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 3A are dissolved in 330 ml of THF, and 27 g (341 mmol) of pyridine are added. Then, over the course of 10 minutes, 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 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 1N hydrochloric acid, dried with magnesium sulphate 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 1N hydrochloric acid
  4. dry with materialdried with magnesium sulphate
  5. concentrationconcentrated in a rotary evaporator

Sources & evidence

ORD record
ord-aa7c50844f5a4f9eb27ac5a42c48c6cf
Source dataset
uspto-grants-2007_02
Patent number
US07173037B2

Reaction notes

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