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

HRID 2271056Notes

Reaction equation

HRID 2271056 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][N:8]=1.[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]>>[CH3:13][C:10]1[CH:11]=[CH:12][C:7]([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:8][CH:9]=1

Participants

4

Reactant 3

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

Product 1

HCID 111327115-Methyl-2-(tri-n-butylstannyl)pyridineYield 58.4%

Procedure

n-Butyllithium (12.8 ml, 2.5M in hexanes, 32.6 mmol) was added dropwise to a cooled (−78° C.) solution of 2-bromo5-methylpyridine (5.0 g, 29.1 mmol), and the solution stirred for an hour. Tri-n-butyltin chloride (9.5 ml, 34.9 mmol) was then added and the reaction allowed to warm to room temperature, and stirred for 18 hours. The reaction mixture was evaporated under reduced pressure and the residue purified by column chromatography on silica gel using an elution gradient of pentane:ethyl acetate (100:0 to 90:10) to give the title compound, (6.5 g, 58%) as a yellow oil.

Workup

  1. stirringstirred for 18 hours
  2. customThe reaction mixture was evaporated under reduced pressure
  3. customthe residue purified by column chromatography on silica gel using an elution gradient of pentane:ethyl acetate (100:0 to 90:10)

Sources & evidence

ORD record
ord-351c764915194134b4338b2a1f07538e
Source dataset
uspto-grants-2001_12
Patent number
US06333330B1

Reaction notes

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