Tributyltin Chloride → 5-Methyl-2-(tri-n-butylstannyl)pyridine

HRID 1174238Notes

Reaction equation

HRID 1174238 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.C([Li])CCC.[CH2:14]([Sn:18](Cl)([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][CH2:16][CH3:17]>CCOCC>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([Sn:18]([CH2:19][CH2:20][CH2:21][CH3:22])([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:14][CH2:15][CH2:16][CH3:17])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 5642162-Bromo-5-methylpyridineHCID 178418339Butyllithium

Product 1

HCID 111327115-Methyl-2-(tri-n-butylstannyl)pyridine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

A solution containing 2-bromo-5-methylpyridine (1.42 g, 8.23 mmol) in ether (15 mL) at −78° C. was treated with n-butyllithium (5.14 mL, 1.6 M in hexanes) dropwise, stirred at −78° C. for 1 hour, treated with tributyltin chloride (3.35 mL, 12.35 mmol), stirred at 0° C. for 4 hours, quenched with saturated ammonium chloride solution and partitioned between ether and water. The organic phase was washed with brine and dried over MgSO4, filtered and concentrated. The residue was purified by chromatography on neutral alumina eluting with 10% ethyl acetate in dichloromethane to give the title compound.

Workup

  1. stirringstirred at 0° C. for 4 hours
  2. customquenched with saturated ammonium chloride solution
  3. custompartitioned between ether and water
  4. washThe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on neutral alumina eluting with 10% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-881f86760d1e4af1ad3ce9f0d54ea58d
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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