4-Fluorophenylboronic acid → 1-ethyl-6-(4-fluorophenyl)-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile

HRID 2373242Notes

Reaction equation

HRID 2373242 reaction equation
FC(F)(F)S(O[C:7]1[N:12]=[C:11]2[N:13]([CH2:16][CH3:17])[N:14]=[CH:15][C:10]2=[C:9]([C:18]2[CH:19]=[N:20][CH:21]=[C:22]([CH3:24])[CH:23]=2)[C:8]=1[C:25]#[N:26])(=O)=O.[F:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1.P(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:16]([N:13]1[C:11]2=[N:12][C:7]([C:33]3[CH:34]=[CH:35][C:30]([F:29])=[CH:31][CH:32]=3)=[C:8]([C:25]#[N:26])[C:9]([C:18]3[CH:19]=[N:20][CH:21]=[C:22]([CH3:24])[CH:23]=3)=[C:10]2[CH:15]=[N:14]1)[CH3:17]

Participants

7

Reactant 3

HCID 2856454-Fluorophenylboronic acidHCID 866024005-cyano-1-ethyl-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridin-6-yl trifluoromethanesulfonateHCID 178527066HCID 178527066, compound

Product 1

HCID 691847921-ethyl-6-(4-fluorophenyl)-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridine-5-carbonitrileYield 79.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 5-cyano-1-ethyl-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridin-6-yl trifluoromethanesulfonate (253 mg), 4-fluorobenzeneboronic acid (129 mg), powdered potassium phosphonate (195 mg) in 1,4-dioxane (4 ml) was added tetrakis(triphenylphosphine)palladium(0) (18 mg) at room temperature. The mixture was refluxed for 7 hours. Resulting mixture was diluted with EtOAc (10 ml), washed with water (×2) and brine and dried over MgSO4. The solvent was evaporated and the residue was purified with silica gel column chromatography to give 1-ethyl-6-(4-fluorophenyl)-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile (175 mg) as colorless solid.

Workup

  1. temperatureThe mixture was refluxed for 7 hours
  2. customResulting mixture
  3. washwashed with water (×2) and brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was evaporated
  6. customthe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-3c0e0375613a4bca9215a2871f69f50b
Source dataset
uspto-grants-2008_12
Patent number
US07459451B2

Reaction notes

Loading…