Water → HCID 90150838, compound

HRID 1844681Notes

Reaction equation

HRID 1844681 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[N:5]=[C:4]([OH:12])[CH:3]=1.[H-].[Na+].[C:15]([CH2:19]OS(C1C=CC(C)=CC=1)(=O)=O)([F:18])([F:17])[F:16].O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([O:12][CH2:19][C:15]([F:18])([F:17])[F:16])[N:5]=[C:6]([C:8]([CH3:9])([CH3:11])[CH3:10])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 67942Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate)HCID 178440592HCID 178440592, compound

Product 1

HCID 90150838HCID 90150838, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-bromo-6-(tert-butyl)pyridin-2-ol (5.00 g, 21.8 mmol) in dry DMF (50 mL) was added NaH (1.75 g, 43.7 mmol) at 0° C. under N2 and the mixture was stirred at 0° C. for 30 min. Then CF3CH2OTs (11.1 g, 43.7 mmol) was added and the solution was stirred at 70° C. overnight. Water was added and the mixture was extracted with EA twice. The combined organic layers were washed with water (3×) and brine twice, concentrated and purified by CC (PE/EA=30/1) to give compound P2a (1.13 g, 17%) as a white oil.

Workup

  1. stirringthe solution was stirred at 70° C. overnight
  2. extractionthe mixture was extracted with EA twice
  3. washThe combined organic layers were washed with water (3×) and brine twice
  4. concentrationconcentrated
  5. custompurified by CC (PE/EA=30/1)
  6. customto give compound P2a (1.13 g, 17%) as a white oil

Sources & evidence

ORD record
ord-94b01b1a8d164fb985ff5323679cbb5a
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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