Benzenesulfonyl chloride → HCID 59023876, compound

Participants

Reaction Steps

1-Bromo-pyrrolidine-2,5-dione (5.34 g, 30 mmol) was added to a stirred solution of N,N-dimethyl-N′-(1H-pyrrolo[2,3-c]pyridin-5-yl)-formamidine (Preparation #10b, 6.00 g, 31.9 mmol) in DMF (200 mL) at about 0° C. The reaction was allowed to warm to ambient temperature then stirred for about 1 hour. Benzenesulfonyl chloride (3.83 mL, 30.0 mmol) and Na2CO3 (6.36 g, 60.0 mmol) were added and the mixture was warmed at about 60° C. for about 1 hour. The reaction mixture was concentrated under reduced pressure and the dark solids were triturated with EtOAc (2×100 mL) and filtered. The combined EtOAc layers were passed through a 6 inch silica gel column, eluting with EtOAc. The product fractions were combined and concentrated to yield N′-(1-benzenesulfonyl-3-bromo-1H-pyrrolo[2,3-c]pyridin-5-yl)-N,N-dimethylformamidine (4.29 g, 35%) as a tan solid. RP HPLC (Table 1, Method e) Rt=2.18, m/z: (MH)+ 407/409.

Provenance & Evidence