Phosgene → 2-isocyanato-5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-benzamide

Participants

Reaction Steps

A 50 mL round bottomed flask was charged with 2-amino-5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-benzamide (500 mg, 0.926 mmol), methylene chloride (10 mL) and saturated sodium bicarbonate solution (10 mL). The solution was cooled in an ice-water bath for 5 min. Phosgene (2.5 mL, 20% w/w solution in toluene) was added to the mixture. The solution was stirred rapidly for 30 minutes. The ice-bath was removed, and the reaction mixture was stirred for an additional 30 minutes. The layers were separated and the aqueous layer was extracted twice with methylene chloride. The combined organic fractions were dried over sodium sulfate, filtered, and concentrated. The residue was triturated with anhydrous ether to give 457 mg (081 mmol, 87%) of 2-isocyanato-5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-benzamide, which was used directly without any further purification or characterization in the subsequent step.

Provenance & Evidence