3-Pyridinecarboxaldehyde → HCID 11264150, compound

HRID 392837Notes

Reaction equation

HRID 392837 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[O:8])[CH:2]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([Mg]Br)=[CH:12][CH:11]=1>O1CCCC1.CCOCC>[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[OH:8])=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 103713-PyridinecarboxaldehydeHCID 178418676HCID 178418676, compound

Product 1

HCID 11264150HCID 11264150, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3-pyridinecarboxaldehyde (5.32 g, 49.7 mmol) in tetrahydrofuran (100 ml) was cooled to-78° C. and treated dropwise with 25 ml (50 mmol) of a 2 M solution of 4-fluorophenyl magnesium bromide in ether. The reaction mixture was then slowly warmed up to 0° C. over 1 h and then quenched by the addition of saturated aqueous sodium bicarbonate and ethyl acetate. The organic phase was washed with brine, dried (magnesium sulfate) and concentrated under reduced pressure. Filtration of the residue on a short silica gel pad (elution ethyl acetate) followed by distillation in vacuo gave 9.42 g (93%) of the title material as a clear oil which crystallized upon standing. bp 120-130° C./0.2 torr (bulb to bulb distillation, air bath temperature), mp 45-47° C. 1HNMR 400 MHz (CDCl3) δ (ppm): 5.88 (1H, s, CH benzhydryl), 7.05 (2H, m, aromatics), 7.25-7.36 (3H, m, aromatics), 7.73 (1H, d, J=7.9 Hz, aromatic), 8.44 (1H, d, J=5.2 Hz, aromatic), 8.55 (1H, s, aromatic). Anal. Calcd for C12H10FNO: C, 70.92; H, 4.96; N, 6.89. Found: C, 70.61; H, 4.86; N, 6.71.

Workup

  1. customquenched by the addition of saturated aqueous sodium bicarbonate and ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated under reduced pressure
  5. filtrationFiltration of the residue
  6. washon a short silica gel pad (elution ethyl acetate)
  7. distillationfollowed by distillation in vacuo

Sources & evidence

ORD record
ord-f451b16390a5411ab68589731e14e3f6
Source dataset
uspto-grants-2004_10
Patent number
US06803378B2

Reaction notes

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