Toluene → HCID 67453941, compound

HRID 2276780Notes

Reaction equation

HRID 2276780 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[F:9][C:10]1([F:16])[CH2:13][CH:12]([C:14]#[N:15])[CH2:11]1.C1(C)C=CC=CC=1.C[Si](C)(C)[N-][Si](C)(C)C.[Na+]>CCOC(C)=O.O>[Cl:8][C:7]1[C:2]([C:12]2([C:14]#[N:15])[CH2:13][C:10]([F:16])([F:9])[CH2:11]2)=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 169882,3-DichloropyridineHCID 2724254Sodium bis(trimethylsilyl)amideHCID 130823913,3-Difluorocyclobutane-1-carbonitrile

Product 1

HCID 67453941HCID 67453941, compoundYield 82.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 100 mL round bottom flask was added 2,3-dichloropyridine (2.9 g, 20 mmol), 3,3-difluorocyclobutanecarbonitrile (2.1 g, 18 mmol), and toluene (50 mL). The mixture was cooled to ° C. and sodium hexamethyldisilazide (NaHMDS, 2.0 M in THF, 11 mL, 22 mmol) was added. The reaction mixture was warmed to rt and stirred for 2 h. The mixture was then diluted with EtOAc (20 mL) and water (20 mL). The aqueous layer was extracted with EtOAc and the combined organic phases were washed with brine, dried over Na2SO4, and concentrated to provide the desired product (3.4 g) as a colorless oil.

Workup

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

Sources & evidence

ORD record
ord-5c695bf676544a5180d487d71bd2ef39
Source dataset
uspto-grants-2015_09
Patent number
US09133123B2

Reaction notes

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