4-(4-Chloro-2-fluorophenyl)nicotinaldehyde → 1-(4-(4-Chloro-2-fluorophenyl)pyridin-3-yl)prop-2-en-1-ol

HRID 870908Notes

Reaction equation

HRID 870908 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH:14]=[O:15])=[CH:12][N:11]=[CH:10][CH:9]=2)=[C:4]([F:16])[CH:3]=1.[CH:17]([Mg]Br)=[CH2:18]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][N:11]=[CH:12][C:13]=2[CH:14]([OH:15])[CH:17]=[CH2:18])=[C:4]([F:16])[CH:3]=1

Participants

4

Reactant 2

HCID 866958904-(4-Chloro-2-fluorophenyl)nicotinaldehydeHCID 178418507HCID 178418507, compound

Product 1

HCID 866959021-(4-(4-Chloro-2-fluorophenyl)pyridin-3-yl)prop-2-en-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-(4-chloro-2-fluorophenyl)nicotinaldehyde (0.5 g, 2.122 mmol) (prepared as in Example 5, Part B) in THF (25 mL) at −70° C. was added vinylmagnesium bromide (1.0 M in THF) (6.37 mL, 6.64 mmol) dropwise and the solution was stirred at this temperature for 45 min. The reaction was quenched with saturated aqueous ammonium chloride solution (20 mL) and extracted with ethyl acetate (2×15 mL). The combined organic extracts were washed with brine (1×15 mL), dried over sodium sulfate and concentrated under reduced pressure. The crude product was used without purification in the next step. LCMS (ESI) m/e 264 [(M+H)+, calcd for C14H12ClFNO 264.0]; LC/MS retention time (Method C): tR=1.59 min.

Workup

  1. customThe reaction was quenched with saturated aqueous ammonium chloride solution (20 mL)
  2. extractionextracted with ethyl acetate (2×15 mL)
  3. washThe combined organic extracts were washed with brine (1×15 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was used without purification in the next step

Sources & evidence

ORD record
ord-95339ea150ac45cda93cd48f610434c1
Source dataset
uspto-grants-2015_03
Patent number
US08969564B2

Reaction notes

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