CC1(C)C(C)(C)OB([C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[C:33]5[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=5[C:27]5[C:22]4=[CH:23][CH:24]=[CH:25][CH:26]=5)=[CH:17][CH:16]=3)=[N:13][CH:14]=2)O1.Br[C:36]1[CH:37]=[CH:38][C:39]([C:42]2[N:46]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C:45]3[CH:53]=[CH:54][CH:55]=[CH:56][C:44]=3[N:43]=2)=[N:40][CH:41]=1.C([O-])([O-])=O.[Na+].[Na+].O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.CC(C)=O.C(Cl)Cl.C1COCC1>[C:47]1([N:46]2[C:45]3[CH:53]=[CH:54][CH:55]=[CH:56][C:44]=3[N:43]=[C:42]2[C:39]2[N:40]=[CH:41][C:36]([C:9]3[CH:14]=[N:13][C:12]([C:15]4[CH:16]=[CH:17][C:18]([N:21]5[C:22]6[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=6[C:28]6[C:33]5=[CH:32][CH:31]=[CH:30][CH:29]=6)=[CH:19][CH:20]=4)=[CH:11][CH:10]=3)=[CH:37][CH:38]=2)[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1Following the procedure for 19, 7 (0.757 g, 1.70 mmol), 13 (0.594 g, 1.70 mmol), tetrakis(triphenylphosphine)palladium(0) (98 mg, 85 μmol), Na2CO3 (1.59 g, 15.0 mmol), H2O (15 mL) and THF (25 mL) yielded 21 (0.70 g, 70% yield) as a light yellow solid after flash chromatography (SiO2, 100% CH2Cl2 to 19:1 CH2Cl2-acetone).
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