ClN1C(=O)CCC1=O.[CH3:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[SH:16].[CH2:17]([O:19][C:20]([C:22]1[NH:23][C:24]2[C:29]([CH:30]=1)=[CH:28][C:27]([O:31][CH3:32])=[C:26]([O:33][CH3:34])[CH:25]=2)=[O:21])[CH3:18]>ClCCl>[CH2:17]([O:19][C:20]([C:22]1[NH:23][C:24]2[C:29]([C:30]=1[S:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH3:9])=[CH:28][C:27]([O:31][CH3:32])=[C:26]([O:33][CH3:34])[CH:25]=2)=[O:21])[CH3:18]To a −78° C. solution of dichloromethane (30mL) and N-chlorosuccinimide was added 2-methyl benzenethiol (0.709 mL, 6.01 mmol) dropwise. The reaction was allowed to warm 0° C. and then stirred for 30 minutes. 5,6-dimethoxy-1H-indole-2-carboxylic acid ethyl ester (Lancaster Synthesis Inc., Windham, N.H.) (1.5 g, 6.01 mmol) was added drop wise in dichloromethane (15 mL). The reaction was allowed to warm to room temperature and stirred overnight. The reaction was concentrated under reduced pressure. Methanol (5 mL) was added to the residue and a solid formed. The solid was collected, washed with diethyl ether (20 mL) and air dried to yield a beige solid (1.46 g, 66%). MS: M+−1=370.2 Da.
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