COC(=O)[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[C:13](OC)=[O:14])Br.[OH:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[C:21]#[N:22].C(N(CC)CC)C>CC#N>[Cl:12][C:9]1[CH:8]=[C:7]2[C:6]([C:4]3[O:18][C:19]4[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=4[C:21]=3[N:22]=[C:13]2[OH:14])=[CH:11][CH:10]=1A mixture of 19A (crude, 20.29 mmol) and 2-hydroxy-benzonitrile (20.29 mmol) in MeCN (100 mL) was stirred at room temperature. To the solution was added triethylamine (TEA, 20.44 g, 202.9 mmol) dropwise. After addition completed, the reaction was refluxed for 24 hours, then cooled. The precipitated solids were collected by filtration, washed with a small amount of MeCN, then washed with water several times until there was no TEA salt, dried to give pure product 19B (3.1 g).
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