2-Bromo-5-(trifluoromethyl)pyridine → HCID 58933992, compound

HRID 854344Notes

Reaction equation

HRID 854344 reaction equation
[CH:1]([Mg]Br)=[CH2:2].Br[C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][N:7]=1>C1COCC1.[Cl-].[NH4+].[Br-].[Zn+2].[Br-].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:1]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][N:7]=1)=[CH2:2]

Participants

7

Reactant 2

HCID 27364342-Bromo-5-(trifluoromethyl)pyridineHCID 178418507HCID 178418507, compound

Product 1

HCID 58933992HCID 58933992, compound

Reagents, catalysts & solvents 4

HCID 10421208Zinc bromideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×HCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of vinylmagnesium bromide in THF (1M, 7.38 mL, 7.38 mmol) in THF (29 mL) was added anhydrous zinc bromide (1.66 g, 7.38 mmol) at −78° C. After one hour at this temperature, the mixture was warmed to room temperature. After one hour, tetrakis(triphenylphosphine)palladium(0) (147 mg) and 2-bromo-5-trifluoromethylpyridine (1 g, 4.42 mmol) were added and the mixture heated at 50° C. for 5.25 hours. The mixture was diluted with ammonium chloride solution (10%, 29 mL) and extracted with ethyl acetate (70 mL×2). The combined organic extracts were dried over magnesium sulphate, evaporated and purified by column chromatography (SPE column, silica), eluting with cyclohexane, followed by cyclohexane/ethyl acetate (95:5 v/v), then (9:1 v/v). This afforded the title compound.

Workup

  1. waitAfter one hour
  2. temperaturethe mixture heated at 50° C. for 5.25 hours
  3. extractionextracted with ethyl acetate (70 mL×2)
  4. dry with materialThe combined organic extracts were dried over magnesium sulphate
  5. customevaporated
  6. custompurified by column chromatography (SPE column, silica)
  7. washeluting with cyclohexane

Sources & evidence

ORD record
ord-88b12a52f8cc400b9a8525bb45855bea
Source dataset
uspto-grants-2007_08
Patent number
US07259163B2

Reaction notes

Loading…