Water → HCID 86670208, compound

HRID 2046243Notes

Reaction equation

HRID 2046243 reaction equation
C(NC(C)C)(C)C.[Br:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N:10]=1.Br[CH2:17][CH:18]([CH3:20])[CH3:19].O>C1COCC1>[Br:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:17][CH:18]([CH3:20])[CH3:19])[N:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 65551-Bromo-2-methylpropaneHCID 7912DiisopropylamineHCID 792052-Bromo-6-methylpyridine

Product 1

HCID 86670208HCID 86670208, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 2.5M solution of n-buthyllithium (0.44 mL, 1.1 mmol) was added dropwise to a stirred solution of diisopropylamine (0.16 mL, 1.15 mmol) in THF (2 mL) at −78° C. The mixture was stirred for 15 minutes and 2-bromo-6-methylpyridine (0.11 mL, 1 mmol) was added dropwise. The mixture was stirred for 15 minutes and 1-bromo-2-methylpropane (0.21 mL, 2 mmol) was added dropwise. The mixture was stirred for 1 hour at this temperature and at room temperature for 60 hours. The mixture was treated with water and extracted with AcOEt. The organic layer was separated, dried (MgSO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in heptane 0/100 to 10/90). The desired fractions were collected and the solvents evaporated in vacuo to yield 2-bromo-6-(3-methyl-butyl)-pyridine (82 mg, 36% yield) as a colourless oil.

Workup

  1. stirringThe mixture was stirred for 15 minutes
  2. stirringThe mixture was stirred for 1 hour at this temperature and at room temperature for 60 hours
  3. extractionextracted with AcOEt
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvents evaporated in vacuo
  8. customThe crude product was purified by flash column chromatography (silica; AcOEt in heptane 0/100 to 10/90)
  9. customThe desired fractions were collected
  10. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-d458238eb06d4840b9ebe847ed615daf
Source dataset
uspto-grants-2013_11
Patent number
US08592422B2

Reaction notes

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