Water → HCID 86678193, compound

HRID 1747537Notes

Reaction equation

HRID 1747537 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([OH:13])[C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.FC(F)(F)S(O[Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])(=O)=O.O>ClCCl>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([O:13][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[C:9]([F:11])([F:12])[F:10])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 866781941350349-65-3

Product 1

HCID 86678193HCID 86678193, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In dichloromethane (50 mL) was dissolved 1-(2-bromopyridin-4-yl)-2,2,2-trifluoroethanol (5.00 g, 19.5 mmol) obtained in Step 1. Triethylamine (10.2 mL, 73.2 mmol) and tert-butyldimethylsilyl trifluoromethanesulfonate (7.41 mL, 32.3 mmol) were added under ice-cooling and the mixture was stirred at room temperature for 9.5 hours. Water was added to the reaction mixture. Extraction with ethyl acetate and drying over anhydrous magnesium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1) to give 2-bromo-4-(1-(tert-butyldimethylsilyloxy)-2,2,2-trifluoroethyl)pyridine (6.43 g, 89% yield).

Workup

  1. temperaturecooling
  2. extractionExtraction with ethyl acetate
  3. dry with materialdrying over anhydrous magnesium sulfate
  4. filtrationAfter filtration
  5. customthe solvent in the filtrate was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-af6fd41557804f1abb19bef187e0a62f
Source dataset
uspto-grants-2015_10
Patent number
US09150569B2

Reaction notes

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