Toluene → HCID 67452252, compound

HRID 2276772Notes

Reaction equation

HRID 2276772 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[N:3]=1.[CH:9]1([C:13]#[N:14])[CH2:12][CH2:11][CH2:10]1.C1(C)C=CC=CC=1.C[Si](C)(C)[N-][Si](C)(C)C.[Na+]>CCOC(C)=O.O>[F:8][C:4]1[N:3]=[C:2]([C:9]2([C:13]#[N:14])[CH2:12][CH2:11][CH2:10]2)[CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 739342,6-DifluoropyridineHCID 78148CyanocyclobutaneHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 67452252HCID 67452252, compoundYield 64.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 0° C. solution of 2,6-difluoropyridine (5.0 g, 43 mmol), cyclobutanecarbonitrile (3.5 g, 43 mmol), and toluene (100 mL) was added sodium hexamethyldisilazide (NaHMDS, 2.0 M in THF, 24 mL, 47 mmol). The resulting mixture was warmed to rt and stirred for 2 h. The mixture was then diluted with EtOAc (200 mL) and water (100 mL). The aqueous layer was extracted with EtOAc and the combined organic phases were washed with brine, dried over Na2SO4, concentrated, and purified using silica gel chromatography to provide the desired product (4.9 g) as a colorless oil.

Workup

  1. extractionThe aqueous layer was extracted with EtOAc
  2. washthe combined organic phases were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. custompurified

Sources & evidence

ORD record
ord-ef27d146d5854bec9a84ff56ed692c77
Source dataset
uspto-grants-2015_09
Patent number
US09133123B2

Reaction notes

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