Tributyltin Chloride → 2-Methyl-5-(tributylstannyl)pyridine

HRID 1174254Notes

Reaction equation

HRID 1174254 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N:6][CH:7]=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:4]=[CH:3][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])=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 12010205-Bromo-2-methylpyridineHCID 178418339Butyllithium

Product 1

HCID 183293632-Methyl-5-(tributylstannyl)pyridineYield 111.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

A solution containing 5-bromo-2-methylpyridine (1.2 g, 6.98 mmol) in ether (14 mL) at −78° C. was treated with n-butyllithium (5.2 mL, 1.6 M in hexanes) dropwise, stirred at −78° C. for 1 hour, treated with tributyltin chloride (2.25 mL, 8.30 mmol), stirred at −78° C. for 0.5 hours, and then at 0° C. for 0.5 hours. The reaction was quenched with saturated ammonium chloride solution and the reaction was partitioned between ether and water, and the organic phase was washed with brine and dried over MgSO4, filtered and concentrated to give the title compound (2.97 g), which was used without further purification.

Workup

  1. stirringstirred at −78° C. for 0.5 hours
  2. waitat 0° C. for 0.5 hours
  3. customThe reaction was quenched with saturated ammonium chloride solution
  4. customthe reaction was partitioned between ether and water
  5. washthe organic phase was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-8a4f1a4776e84b4fbd70077ef3366af6
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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