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

Participants

Reaction Steps

Methyl 3-{[2-(5-promo-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.

Provenance & Evidence