Tetrahydrofuran → 5-(Pyrrolidin-1-ylsulfonyl)indoline-2,3-dione

Participants

Reaction Steps

To a cold solution of 2,3-dioxo-2,3-dihydro-1H-indole-5-sulfonylchloride (2.00 g, 8.14 mmol) in a 1:1 mixture of THF: CHCl3 (96 mL) was added drop-wise via syringe pump over a period of 1 hr a solution of pyrrolidine (0.885 mL, 10.6 mmol) and N,N-diisopropylethyl amine (2.84 mL, 16.3 mmol, 2 eq) in chloroform (16 mL) under a dry N2 atmosphere with cooling in an ice bath. After stirring for 1 h., the reaction was concentrated. The crude product was purified on Biotage KP silica gel eluting with 80/20 CH2Cl2/EtOAc to give the title compound as a greenish-yellow solid (0.88 g, 39% yield). NMR (300 Mz, DMSO-d6): consistent. MS: (ES−) m/z 279 [M−H].

Provenance & Evidence