[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([NH2:9])=[C:4](I)[CH:3]=1.[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]#[CH:19]>>[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([NH2:9])=[C:4]([C:19]#[C:18][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[Cl:11])[CH:3]=1The title compound was prepared in analogy to example 10 step A from 4-chloro-2-iodo-6-methyl-phenylamine (1.5 g, 5.61 mmol) and 1-chloro-2-ethynyl-benzene (920 mg, 6.73 mmol) to afford 4-chloro-2-(2-chloro-phenylethynyl)-6-methyl-phenylamine (1.06 g, 68%) as an off white solid. LC-MS (ESI): 276 (M+H)+.
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