Potassium Carbonate → HCID 58556856, compound

HRID 244280Notes

Reaction equation

HRID 244280 reaction equation
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.Br[CH2:10][CH2:11][F:12].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[Br:1][C:2]1[C:7]([O:8][CH2:10][CH2:11][F:12])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 129822-Fluoroethyl bromideHCID 230702-Bromo-3-pyridinol

Product 1

HCID 58556856HCID 58556856, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-bromopyridin-3-ol 27 (0.1 mmol), 1-bromo-2-fluoroethane (0.2 mmol) and K2CO3 (0.4 mmol) in acetonitrile were stirred at refluxing for one day until TLC indicated that the reaction was complete, and then filter, dried and concentrated under reduce pressure. The crude product was purified with column chromatography to afforded 28 (yield, 68%). 1H NMR (CDCl3): δ 4.25-4.34 (m, 2H), 4.73-4.89 (m, 2H), 7.20-7.22 (m, 2H), 8.01 (s, 1H).

Workup

  1. temperatureat refluxing for one day until TLC
  2. filtrationfilter
  3. customdried
  4. concentrationconcentrated
  5. customThe crude product was purified with column chromatography

Sources & evidence

ORD record
ord-ec70ba0f2a72404cb791b478effcf4db
Source dataset
uspto-grants-2014_02
Patent number
US08658131B2

Reaction notes

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