4-Methylpyridine → 1-(3-FLUOROPHENYL)-2-(4-PYRIDYL)ETHANONE

HRID 1710682Notes

Reaction equation

HRID 1710682 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7]CC)=O.[CH3:13][C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1COCC1.CCCCCC>[F:1][C:2]1[CH:3]=[C:4]([C:5](=[O:7])[CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 79634-MethylpyridineHCID 67975Benzoic acid, 3-fluoro-, ethyl esterHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 112528861-(3-FLUOROPHENYL)-2-(4-PYRIDYL)ETHANONEYield 89.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of ethyl 3-fluorobenzoate (2.0 g, 11.9 mmol) and 4-methylpyridine (1.1 mL, 1.0 g, 10.8 mmol) in THF (9 mL) at 0° C. under nitrogen atmosphere was added dropwise lithium bis(trimethylsilyl)amide (23.8 mL, 1.0M in hexane, 23.8 mmol) During the addition a precipitate was formed and the suspension was stirred at room temperature overnight. The reaction was diluted with hexane (40 mL) and filtered. The solid was partitioned between ethyl acetate and a saturated solution of ammonium chloride. The organic phase was dried (MgSO4) and evaporated under reduced pressure to give the title compound as a yellow solid (2.09 g, 82%).

Workup

  1. additionDuring the addition a precipitate
  2. customwas formed
  3. filtrationfiltered
  4. customThe solid was partitioned between ethyl acetate
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-630832ca1323431c94c6a3968013559f
Source dataset
uspto-grants-2010_09
Patent number
US07790728B2

Reaction notes

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