2-Bromopyridine → HCID 86594757, compound

HRID 1592404Notes

Reaction equation

HRID 1592404 reaction equation
[Li+].CC([N-]C(C)C)C.[Br:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.[C:16]1(=[O:21])[CH2:20][CH2:19][CH2:18][CH2:17]1.C([O-])(O)=O.[Na+]>C1COCC1.CCOC(C)=O>[Br:9][C:10]1[C:15]([C:16]2([OH:21])[CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

7

Reactant 4

HCID 79732-BromopyridineHCID 8452CyclopentanoneHCID 516892Sodium BicarbonateHCID 2724682Lithium diisopropylamide

Product 1

HCID 86594757HCID 86594757, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a cold (−78° C.) solution of LDA (24.5 mmol) in dry THF (100 mL) was added 2-bromopyridine (2.0 mL, 20.9 mmol) and the resultant solution was stirred for 90 minutes. Cyclopentanone (4.0 mL, 45.2 mmol) was added and the mixture was stirred for and additional 80 minutes. The mixture was treated with saturated aqueous NaHCO3 (20 mL) and warmed to room temperature. The mixture was diluted with EtOAc (300 mL) and the phases were separated. The organic phase was washed with saturated aqueous NaHCO3 (3×25 mL) and brine (3×25 mL), dried (MgSO4), and concentrated. Purification of the crude material by column chromatography on silica gel (3:1 hexanes-EtOAc) provided 2.00 g (40%) of 1-(2-Bromo-pyridin-3-yl)-cyclopentanol as a yellow oil.

Workup

  1. customthe phases were separated
  2. washThe organic phase was washed with saturated aqueous NaHCO3 (3×25 mL) and brine (3×25 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customPurification of the crude material by column chromatography on silica gel (3:1 hexanes-EtOAc)

Sources & evidence

ORD record
ord-afca57edc61149bd9e74adc622329be9
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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