Water → 1-((2-Fluorophenyl)methyl)pyrazolo(3,4-b)pyridine-3-carbonitrile
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
Conditions
- Temperature
- 40 °C
Procedure
36.1 g (133 mmol) of 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboxamide from Example 22A are dissolved in 330 ml of THF and mixed with 27 g (341 mmol) of pyridine. Over a period of 10 min, 47.76 ml (71.66 g, 341 mmol) of trifluoroacetic anhydride are subsequently added, and the temperature increases to 40° C. during the addition. The mixture is stirred at room temperature overnight. The mixture is subsequently poured into 1 l of water, and the mixture is 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 using a rotary evaporator.
Workup
- extractionthe mixture is extracted three times with 0.5 l of ethyl acetate each time
- washThe organic phase is washed with saturated sodium bicarbonate solution and with 1 N HCl
- dry with materialdried with MgSO4
- concentrationconcentrated
- customa rotary evaporator
Sources & evidence
- ORD record
- ord-5ea9c129f4964750a5b66b4feecba39c
- Source dataset
- uspto-grants-2004_06
- Patent number
- US06743798B1
Reaction notes
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