Réaction #418196

Équation de réaction

4-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine

tert-butyl 3-(tosyloxy)azetidine-1-carboxylate

cesium carbonate

→

title compound

Rendement 32.8%

tert-butyl 3-(4-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridin-1-yl)azetidine-1-carboxylate

Rendement 32.8%

Solvants

DMSO

water

Conditions de réaction

Traitement

1. 1
   Températurethe mixture heated overnight
2. 2
   Extractionextracted with ethyl acetate (50 mL×3)
3. 3
   SéchageThe combined organics were dried over magnesium sulfate
4. 4
   Concentrationconcentrated
5. 5
   AutreThe crude was purified on normal phase silica eluting with ethyl acetate and cyclohexane (0-50%)

Mode opératoire

To a mixture of 4-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine (D6) (500 mg, 1.548 mmol) and tert-butyl 3-(tosyloxy)azetidine-1-carboxylate (D100) (558 mg, 1.703 mmol) in DMSO (10 mL) was added cesium carbonate (1513 mg, 4.64 mmol). The final mixture was heated at 80° C. for 4 hours after which the temperature is increase to 95° C. and the mixture heated overnight. The reaction mixture was diluted with water (50 mL) and then extracted with ethyl acetate (50 mL×3). The combined organics were dried over magnesium sulfate and concentrated. The crude was purified on normal phase silica eluting with ethyl acetate and cyclohexane (0-50%) to give the title compound (243 mg). LCMS (A): m/z (M+H)+ 478/480, C15H17BrIN3O2 requires 477/479 (acidic).

Source