Water → HCID 69290841, compound

HRID 900769Notes

Reaction equation

HRID 900769 reaction equation
[C:1]1([Mg]Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:9][C:10]1[CH:18]=[CH:17][C:13]([C:14](Cl)=[O:15])=[CH:12][N:11]=1.O>CCOCC>[F:9][C:10]1[N:11]=[CH:12][C:13]([C:14]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:15])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 146236022-Fluoropyridine-5-carbonyl chlorideHCID 178478979HCID 178478979, compound

Product 1

HCID 69290841HCID 69290841, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A 3M etheral solution of phenyl magnesium chloride (4.67 ml, 14 mmol) was slowly added at −30° C. to a solution of 6-fluoronicotinoyl chloride (3.35 g, 21 mmol) in ether (25 ml). After complete addition, the cooling bath was removed and the reaction was allowed to reach 10° C. Hydrolysis was performed by addition of water, and the mixture is then diluted with ether. After separation of the layers, the ether solution was washed with brine, dried over Na2SO4 and evaporated in vacuum to yield a yellowish oil. After purification by chromatography on silica gel (CH2Cl2/Hexane 85/15), the (6-fluoro-3-pyridinyl)(phenyl)methanone 39 was obtained as a yellow oil (980 mg, 35%).

Workup

  1. additionAfter complete addition
  2. customthe cooling bath was removed
  3. customto reach 10° C
  4. customHydrolysis
  5. customAfter separation of the layers
  6. washthe ether solution was washed with brine
  7. dry with materialdried over Na2SO4
  8. customevaporated in vacuum
  9. customto yield a yellowish oil
  10. customAfter purification by chromatography on silica gel (CH2Cl2/Hexane 85/15)

Sources & evidence

ORD record
ord-df45e7107cdf49c5af33783560940fa3
Source dataset
uspto-grants-2008_04
Patent number
US07361668B2

Reaction notes

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