1-Bromo-2,2-dimethylpropane → HCID 70873072, compound

HRID 1844686Notes

Reaction equation

HRID 1844686 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[N:8]=[C:7]([OH:9])[CH:6]=[CH:5][CH:4]=1.[H-].[Na+].Br[CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17]>CN(C=O)C>[CH2:15]([O:9][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([C:2]([F:1])([F:10])[F:11])[N:8]=1)[C:16]([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 124151-Bromo-2,2-dimethylpropaneHCID 24758Sodium hydrideHCID 178516021HCID 178516021, compound

Product 1

HCID 70873072HCID 70873072, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-(trifluoromethyl)pyridin-2-ol (5.00 g, 30.7 mmol) in dry DMF (50 mL) was added NaH (3.71 g, 92.1 mmol) under N2 and the mixture was stirred at rt for 1 h. Then 1-bromo-2,2-dimethylpropane (11.6 g, 76.7 mmol) was added and the resulting mixture was heated at 100° C. overnight, cooled, quenched with water (10 mL) and extracted with EA twice. The combined organic layers were washed with brine (3×), concentrated and purified by CC on NH silica gel (PE/EA=100/1) to give compound P12a (1.05 g, 15%) as an oil.

Workup

  1. temperaturethe resulting mixture was heated at 100° C. overnight
  2. temperaturecooled
  3. customquenched with water (10 mL)
  4. extractionextracted with EA twice
  5. washThe combined organic layers were washed with brine (3×)
  6. concentrationconcentrated
  7. custompurified by CC on NH silica gel (PE/EA=100/1)
  8. customto give compound P12a (1.05 g, 15%) as an oil

Sources & evidence

ORD record
ord-33f75df8f848436e861234748df7fcdf
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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