Triphenylphosphine → HCID 22282149, compound

HRID 1062578Notes

Reaction equation

HRID 1062578 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]([CH3:12])[N:9]=[C:10]([CH3:11])[C:5]2=[CH:4][C:3]=1[C:13]#[N:14].[CH:15]([Sn](CCCC)(CCCC)CCCC)=[CH2:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F-].[K+]>C1(C)C=CC=CC=1.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>[CH3:12][N:8]1[C:6]2=[N:7][C:2]([CH:15]=[CH2:16])=[C:3]([C:13]#[N:14])[CH:4]=[C:5]2[C:10]([CH3:11])=[N:9]1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 81998TributylvinyltinHCID 522689Potassium FluorideHCID 22282145769971-54-2

Product 1

HCID 22282149HCID 22282149, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

6-Chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile (2.71 g, 13.1 mmol) was dissolved in toluene (45 mL). Vinyl tributyltin (5 g, 15.8 mmol) and triphenylphosphine (103 mg, 3.93 mmol) were added, followed by Pd(PPh3)4 (151 mg, 0.13 mmol). The reaction mixture was heated at reflux for 2 hours, allowed to cool to room temperature, and then treated with saturated aqueous KF solution for 30 minutes. The precipitated solid (tributyltin fluoride) was removed by filtration. The aqueous layer was separated and extracted with ethyl acetate. The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The residue was washed with hexane to give 1,3-dimethyl-6-vinyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile (2.50 g, 96%) as a pale yellow powder.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 hours
  3. customThe precipitated solid (tributyltin fluoride) was removed by filtration
  4. customThe aqueous layer was separated
  5. extractionextracted with ethyl acetate
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-ed3d9b2e11f742459db1557f35076b12
Source dataset
uspto-grants-2005_11
Patent number
US06962926B2

Reaction notes

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