1-Bromo-2-Chloroethane → 1-(2-Chloroethyl)-n-(thiazol-2-yl)indoline-5-sulfonamide

Participants

Reaction Steps

To a stirring solution of 2,3-dihydro-1H-indole-5-sulfonic acid thiazol-2-ylamide (10.0 g, 35.6 mmol), Et3N (5.0 mL, 3.6 g, 35.6 mmol), and DMF (10.0 mL), under N2, was added 1-bromo-2-chloroethane (2.9 mL, 5.1 grams, 35.6 mmol). The solution was stirred at room temperature for 3 days. The mixture was partitioned between water and ethyl acetate. The organic portion was evaporated to dryness under reduced pressure. The residue was purified via silica gel chromatography using 3% MeOH in CH2Cl2 to obtain the desired amine (3.1 g, 9.0 mmol, 25% yield) as a clear oil. 1H-NMR (DMSO-d6) δ 7.39-7.37 (m, 2H), 6.83 (d, J=4.7 Hz, 1H), 6.43 (d, J=7.3 Hz, 2H), 6.28 (s, 1H), 4.23 (t, J=5.8 Hz, 2H), 3.88 (t, J=5.8 Hz, 2H), 3.47 (t, J=8.7 Hz, 2H), 3.33 (s, 1H), 2.94 (t, J=3.7 Hz, 2H). LC/MS (10-99%) M/Z: M+1 obs=344.0; tR=2.88 min.

Provenance & Evidence