2-Bromopyridine → HCID 15123334, compound

HRID 1840319Notes

Reaction equation

HRID 1840319 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.CCCCCC.[CH2:19]([N:26]1[CH2:31][CH2:30][CH2:29][CH2:28][C:27]1=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C1C[O:36]CC1>>[CH2:19]([N:26]1[CH2:31][CH2:30][C:29]([OH:36])([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 5

HCID 79732-BromopyridineHCID 8028TetrahydrofuranHCID 8058HexaneHCID 51700761-Benzyl-2-piperidoneHCID 178418339Butyllithium

Product 1

HCID 15123334HCID 15123334, compoundYield 66.41%

Procedure

To a stirred solution of 2-bromopyridine (10 mmol) in THF (120 mL) at −78° C. under argon, 2.5 M n-butyl lithium solution in hexane (4.5 mL, 11.25 mmol) was injected over 5 min. After 25 min, 1-benzylpiperidone (10 mmol) was added neat. After 30 min, the mixture was quenched by addition of aqueous NH4Cl solution (50 mL). The mixture diluted with ethyl acetate (200 mL), washed with brine (150 mL), dried (Na2SO4). Solvent was evaporated and the residue was purified by column chromatography (silica gel, EtOAc/Hexane from 20% to 60%) to give the desired product (1.78 g, 66.41%) H-NMR was consistent with the structure.

Workup

  1. waitAfter 30 min
  2. customthe mixture was quenched by addition of aqueous NH4Cl solution (50 mL)
  3. additionThe mixture diluted with ethyl acetate (200 mL)
  4. washwashed with brine (150 mL)
  5. dry with materialdried (Na2SO4)
  6. customSolvent was evaporated
  7. customthe residue was purified by column chromatography (silica gel, EtOAc/Hexane from 20% to 60%)

Sources & evidence

ORD record
ord-7872e9417aa34573b695d5b7d7ce37de
Source dataset
uspto-grants-2004_01
Patent number
US06680323B2

Reaction notes

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