Methanesulfonyl chloride → HCID 58914746, compound

Participants

Reaction Steps

Combine 3-(4-amino-phenyl)-1-(2-chloro-benzyl)-3-(4-methoxy-3,5-dimethyl-phenyl)-1,3-dihydro-indol-2-one (73 mg, 0.15 mmol), N,N-diisopropylethylamine (0.040 mL, 0.23 mmol) and methanesulfonyl chloride (0.013 mL, 0.165 mmol) in CH2Cl2 (1 mL). After 5 h. stirring at room temperature TIC (50% EtOAc/hexanes) shows reaction not complete. Add more N,N-diisopropylethylamine (0.040 mL, 0.23 mmol) and methanesulfonyl chloride (0.013 mL, 0.165 mmol) and stir 2 h. more at which time reaction complete. Dilute with ethyl acetate and wash with water amd brine. Dry (MgSO4), filter and concentrate in vacuo to give 96 mg of a residue. Purify by radial chromatography (step gradient of 10% EtOAc/hexanes, 20% EtOAc/hexanes, 25% EtOAc/hexanes and 33% EtOAc/hexanes to obtain 56 mg (58%) of the title compound. MS (ES): m/z=639 (M+1); 1H NMR(DMSO-d6); δ7.54-7.45 (m, 4H), 7.37-7.22 (m, 5H), 7.15 (t, J=7.5, 1H), 7.00 (m, 2H), 6.87 (s, 2H), 5.09 (s, 2H), 3.64 (s, 3H), 3.53 (s, 6H), 2.17 (s, 6H).

Provenance & Evidence