Methyl iodide → 5-Bromo-2-[2-(methylsulfonyl)propan-2-yl]-1,3-thiazole

HRID 410596Notes

Reaction equation

HRID 410596 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([S:10]([CH2:13]CC(OC)=O)(=[O:12])=[O:11])([CH3:9])[CH3:8])=[N:4][CH:3]=1.C[O-].[Na+].CI>C1COCC1.CS(C)=O.O>[Br:1][C:2]1[S:6][C:5]([C:7]([S:10]([CH3:13])(=[O:11])=[O:12])([CH3:9])[CH3:8])=[N:4][CH:3]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 67258095Methyl 3-{[2-(5-bromo-1,3-thiazol-2-yl)propan-2-yl]sulfonyl}propanoate

Product 1

HCID 672585745-Bromo-2-[2-(methylsulfonyl)propan-2-yl]-1,3-thiazoleYield 93.3%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-{[2-(5-bromo-1,3-thiazol-2-yl)propan-2-yl]sulfonyl}propanoate (Example 70, Step 4, 500 mg, 1.403 mmol) was taken up in THF (15 mL) at room temperature, and NaOMe (25% in MeOH, 303 mg, 1.403 mmol) was added. After 30 min at room temperature, the suspension was evaporated to dryness, providing a white solid. The solid was taken back up in DMSO (5 mL), and methyl iodide (398 mg, 2.81 mmol) was added. After stirring for 2 h at room temperature, the reaction was diluted with water and extracted with ethyl acetate (2×). The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated. Flash chromatography (0-40% ethyl acetate in hexanes) afforded of 5-bromo-2-[2-(methylsulfonyl)propan-2-yl]-1,3-thiazole (372 mg, 93%) as a colorless solid. MS ESI: [M+H]+ m/z 283.9/285.9.

Workup

  1. customthe suspension was evaporated to dryness
  2. customproviding a white solid
  3. extractionextracted with ethyl acetate (2×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-8020b5921b524970b2c12f94f1e07bff
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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