4-Chloropyridine → HCID 10811131, compound

HRID 1455662Notes

Reaction equation

HRID 1455662 reaction equation
[Li+].CC([N-]C(C)C)C.[Cl:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1.[CH2:16]([Sn:20](Cl)([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH3:19]>C1COCC1.O>[Cl:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[Sn:20]([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:16][CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 3

HCID 122884-ChloropyridineHCID 15096Tributyltin ChlorideHCID 2724682Lithium diisopropylamide

Product 1

HCID 10811131HCID 10811131, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of LDA (1.1 eq) in THF (0.05M) at −78° C. was added 4-chloropyridine (1 eq). After 1.5 h tributyltin chloride (1.5 eq) was added and the reaction mixture was warmed at rt over 3 h. The reaction mixture was diluted with water and extracted with EtOAc. The organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (hexane:EtOAc, 95:5) to afforded the title compound.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (hexane:EtOAc, 95:5)

Sources & evidence

ORD record
ord-19acac11b8224020816388efcba942aa
Source dataset
uspto-grants-2009_01
Patent number
US07482456B2

Reaction notes

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