Benzenamine, 2-chloro-4-(methylsulfonyl)- → 2-[3-chloro-5-(3-chloro-5-cyanophenoxy)phenoxy]-N-[2-chloro-4-(methylsulfonyl)phenyl]acetamide

Participants

Reaction Steps

A DMF solution (0.5 mL) of 29 mg (0.081 mmol) of [3-chloro-5-(3-chloro-5-cyanophenoxy)phenoxy]acetyl chloride (5-4), 33 mg (0.163 mmol) of 2-chloro-4-methylsulfonylaniline (5-5) and 21 mg (0.163 mmol) of DIEA were stirred at 25° C. until the reaction would not proceed any further. This solution was loaded directly onto a CombiFlash silica gel column eluted with EtOAc:hexanes (3:97 to 100:0). Clean fractions were combined and concentrated in vacuo to give the desired product 5-6 as a white solid. Rf=0.8 (DCM:MeOH:NH4OH 98:2:0.2). HRMS (M+Na): measured 542.0066; theoretical 542.0105. 1H NMR(CDCl3): 3.07 (s, 3H), 4.69 (s, 2H), 6.61 (m, 1H), 6.74 (m, 1H), 6.89 (m, 1H), 7.15 (m, 1H), 7.25 (m, 1H), 7.42 (m, 1H), 6.94 (dd, 1H), 8.02 (m, 1H), 8.74 (d, 1H), 9.11 (s, 1H).

Provenance & Evidence