Reaction #610654

Reaction equation

water

methyl 5-chloro-1H-pyrrolo[3,2-b]pyridine-2-carboxylate

cesium carbonate

1-bromo-4-fluorobutane

→

methyl 5-chloro-1-(4-fluorobutyl)-1H-pyrrolo[3,2-b]pyridine-2-carboxylate

Solvents

DMF

Conditions

Workup

1. 1
   Temperatureto cool down to room temperature
2. 2
   Extractionthe product was extracted 3 times with DCM
3. 3
   DryingThe combined organic layers were dried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Otherevaporated
6. 6
   Otherto give the targeted product 11-d as a yellowish solid

Procedure

To a solution of methyl 5-chloro-1H-pyrrolo[3,2-b]pyridine-2-carboxylate 11-c (2.9 g, 12.2 mmol) in DMF (50 mL) were added successively cesium carbonate (4 g, 12.2 mmol) and 1-bromo-4-fluorobutane (1.3 mL, 12.2 mmol). The resulting mixture was heated at 60° C. overnight. The reaction mixture was allowed to cool down to room temperature then poured into iced water and the product was extracted 3 times with DCM. The combined organic layers were dried over Na2SO4, filtered and evaporated to give the targeted product 11-d as a yellowish solid. The product was used as such in the next step. m/z=313 (M+H)+, Cl pattern.

Source