Diisopropylethylamine → HCID 58382087, compound

Participants

Reaction Steps

2-(4-Chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-N-methylethanamine (0.670 g, 1.84 mmol) in PrOH (20 mL) was heated to about 105° C. for about 44 h. DIEA (0.39 mL, 2.2 mmol) was added and heating was continued at about 105° C. for about 24 h. The mixture was cooled to rt and the solvent was evaporated under reduced pressure. The material was treated with saturated NaHCO3 (15 mL) and water (10 mL) then extracted with DCM (25 mL then 10 mL). The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated in vacuo. The material was purified by flash chromatography on 10 g of silica with EtOAc as an eluent to give 1-methyl-6-tosyl-1,2,3,6-tetrahydrodipyrrolo[2,3-b:2′,3′-d]pyridine (0.308 g, 51%): LC/MS (Table 2, Method a) Rt=2.53 min; MS m/z 328 (M+H)+.

Provenance & Evidence