4-Chloropyridine → HCID 10811131, compound

HRID 861016Notes

Reaction equation

HRID 861016 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.[Sn:16](Cl)([CH2:25][CH2:26][CH2:27][CH3:28])([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH2:19][CH3:20]>C1COCC1.[NH4+].[Cl-]>[Cl:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[Sn:16]([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:17][CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 3

HCID 122884-ChloropyridineHCID 15096Tributyltin ChlorideHCID 2724682Lithium diisopropylamide

Product 1

HCID 10811131HCID 10811131, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of LDA (1.2 eq.) in THF (0.2M) at −78° C. was added 4-chloro-pyridine (1.0 eq.). The mixture was stirred for 1.5 h at −78° C. then Bu3SnCl (1.5 eq.) was added. The final mixture was slowly warmed to rt, poured in saturated aqueous NH4Cl and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated. Flash chromatography (Hex:EtOAc; 95:5) afforded the title compound as an oil.

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e3f5a46eea24473da35fd8cf1dc29ebe
Source dataset
uspto-grants-2006_12
Patent number
US07153968B2

Reaction notes

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