Dimethyl Disulfide → 2-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-5-methylsulfanyl-pyridine

HRID 83360Notes

Reaction equation

HRID 83360 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:9][C:10]2[C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:12][O:13][C:14]=2[CH3:15])=[N:6][CH:7]=1.C([Li])CCC.[CH3:27][S:28]SC>C1COCC1>[CH3:15][C:14]1[O:13][N:12]=[C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]=1[CH2:9][O:8][C:5]1[CH:4]=[CH:3][C:2]([S:28][CH3:27])=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 12232Dimethyl DisulfideHCID 684448075-Bromo-2-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridineHCID 178418339Butyllithium

Product 1

HCID 426300472-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-5-methylsulfanyl-pyridineYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 5-bromo-2-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridine (300 mg, 0.87 mmol) in THF (3 mL) was added n-butyllithium (1.6 M, 543.1 μL, 0.87 mmol) and the resulting mixture stirred at −78° C. for 30 min. Then methyl disulfide (78.7 μL, 0.87 mmol) was added and the resulting mixture stirred overnight. The mixture was then evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate 8:2 to 1:3) afforded the title compound (136 mg, 50%) as a light yellow oil. MS: m/e=313.1 [M+H]+.

Workup

  1. stirringthe resulting mixture stirred overnight
  2. customThe mixture was then evaporated
  3. customPurification by chromatography (SiO2, heptane:ethyl acetate 8:2 to 1:3)

Sources & evidence

ORD record
ord-f5f2d58ff1254e1eb94986c37c999373
Source dataset
uspto-grants-2014_09
Patent number
US08846719B2

Reaction notes

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