1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 59490916, compound

Participants

Reaction Steps

1-(2-Fluoro-benzyl)-3-(2-methoxy-pyridin-3-yl)-5-methyl-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid B5 (100 mg, 0.25 mmol) was diluted with tetrahydrofuran (3 mL) and to the resulting solution was added carbonyl diimidazole (62 mg, 0.38 mmol). The resulting suspension was heated to reflux and allowed to stir at this temperature for 1 hour. The reaction mixture was cooled to room temperature and cyclopropanesulfonamide (46 mg, 0.38 mmol) and 1,8-diazabicyclo(5.4.0)undec-7-ene (76 mg, 0.5 mmol) was added. The resulting reaction was stirred at room temperature for an additional 14 hours, then concentrated in vacuo. The residue obtained was diluted with ethyl acetate (100 mL) and water (10 mL). The organic layer was separated and the aqueous layer extracted twice more with ethyl acetate (2×20 mL). The combined organic layers were dried (magnesium sulfate), filtered and concentrated in vacuo to provide a crude residue which was purified using flash chromatography to provide cyclopropanesulfonic acid [1-(2-fluoro-benzyl)-3-(2-methoxy-pyridin-3-yl)-5-methyl-1H-pyrrolo[3,2-b]pyridine-2-carbonyl]-amide B6 (0.09 g, 72% yield). MS: 495.3 (M+H)+.

Provenance & Evidence