Trifluoroacetic acid → 3-(Naphthalen-2-yl)-1H-pyrazolo[4,3-b]pyridine-5-carbonitrile

HRID 34003Notes

Reaction equation

HRID 34003 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[C:15]2=[N:16][C:17]([C:20]#[N:21])=[CH:18][CH:19]=[C:14]2[N:13](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:12]=1.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>ClCCl>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[C:15]2=[N:16][C:17]([C:20]#[N:21])=[CH:18][CH:19]=[C:14]2[NH:13][N:12]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 230702263-naphthalen-2-yl-1-trityl-1H-pyrazolo[4,3-b]pyridine-5-carbonitrile

Product 1

HCID 230701243-(Naphthalen-2-yl)-1H-pyrazolo[4,3-b]pyridine-5-carbonitrileYield 94.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 10 mL of a solution containing 360 mg of 3-naphthalen-2-yl-1-trityl-1H-pyrazolo[4,3-b]pyridine-5-carbonitrile obtained by Production example 15 in dichloromethane, 3 mL of trifluoroacetic acid was added at room temperature and stirred for 2 hours. The reaction solution was added with aqueous sodium hydrogen carbonate, extracted with ethyl acetate, washed with water, and dried over magnesium sulfate. After evaporating, the residue was purified and separated by silica gel column chromatography (ethyl acetate:n-hexane=3:1), to afford 180 mg of the title compound as a colorless powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. customAfter evaporating
  5. customthe residue was purified
  6. customseparated by silica gel column chromatography (ethyl acetate:n-hexane=3:1)

Sources & evidence

ORD record
ord-02594a7a820b48c7a022f86fea160b3e
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

Loading…