Br[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1.[C:17]1(B(O)O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CC1C=CN=CC=1C1C=CC=C2C=1C=NN2>>[N+:14]([C:11]1[CH:12]=[CH:13][C:8]([C:3]2[CH:4]=[N:5][CH:6]=[CH:7][C:2]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:9][CH:10]=1)([O-:16])=[O:15]Intermediate 13B was prepared from Intermediate 13A and phenylboronic acid by the procedure described for the preparation of Intermediate 1C. The crude material was purified by silica gel chromatography (12 g ISCO column, eluting with 0 to 40% EtOAc in CH2Cl2) to yield Intermediate 13B. MS (ES): m/z=277.0 [M+H]+.
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