2-Chloro-4-(trifluoromethyl)pyridine → HCID 19392517, compound

HRID 1755985Notes

Reaction equation

HRID 1755985 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][N:3]=1.[CH2:12]([O:14][C:15]([Sn](CCCC)(CCCC)CCCC)=[CH2:16])[CH3:13].[F-].[K+]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:15]([O:14][C:12]([C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][N:3]=1)=[CH2:13])[CH3:16]

Participants

6

Reactant 3

HCID 1449582-Chloro-4-(trifluoromethyl)pyridineHCID 522689Potassium FluorideHCID 619414Stannane, tributyl(1-ethoxyethenyl)-

Product 1

HCID 19392517HCID 19392517, compoundYield 39.1%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-chloro-4-trifluoromethylpyridine (3.33 g), (1-ethoxyvinyl)tri-n-butyltin (5.95 g) and bis(triphenylphosphine)palladium(II) chloride (0.4 g) in DMF (40 ml) was heated at 70° C. for 16 hours. The reaction mixture was cooled to room temperature, potassium fluoride (60 ml of a 10% aqueous solution) was added and the resulting mixture was stirred for 1 hour then filtered through Hyflo supercel filter aid which was rinsed through with ether. The filtrate was extracted with ether (×2) and the combined extracts were washed with brine, then dried, concentrated and chromatographed using ether:hexane 1:4 as the eluant to give 1-ethoxy-1-(4-trifluoromethylpyrid-2-yl)-ethylene (1.4 g, 35% yield) as a pale yellow liquid; 1H NMR (270 MHz): δ1.45(3H,t), 4.00(2H,q), 4.42(1H,d), 5.50(1H,d), 7.40(1H,d), 7.88(1H,s), 8.72(1H,d) ppm.

Workup

  1. filtrationthen filtered through Hyflo supercel
  2. filtrationfilter aid which
  3. washwas rinsed through with ether
  4. extractionThe filtrate was extracted with ether (×2)
  5. washthe combined extracts were washed with brine
  6. customdried
  7. concentrationconcentrated
  8. customchromatographed

Sources & evidence

ORD record
ord-3f19573b170b4f458f143c10bf57f3e8
Source dataset
uspto-grants-1995_08
Patent number
US05439910

Reaction notes

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