[Cl:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N:11]=[C:12]=[S:13])[NH:4][C:3]1=O.C1C=C(OC(OC2N=CC=CC=2)=S)N=CC=1.NC1C=CC=C2C=1C(Cl)=CN2>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N:11]=[C:12]=[S:13])[NH:4][CH:3]=13-Chloro-4-isothiocyanatooxindole. 4-Dimethylaminopyridine (0.031 g, 0.256 mmol) and di-2-pyridyl thionocarbonate (0.983 g, 4.23 mmol) are added to a solution of 4-amino-3-chloroindole (0.655 g, 2.82 mmol) in methylene chloride. The resulting mixture is stirred at room temperature for 1 hour. The volatile organics are removed by rotary evaporation and the crude residue is purified via silica gel column chromatography using 20% ethyl acetate/hexanes as the eluent. The appropriate fractions are combined and the solvents removed by rotary evaporation to yield 0.511 g of 3-chloro-4-isothiocyanatoindole as a yellow solid (96%).
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