Br[C:2]1[C:3]([CH2:20][CH2:21][CH2:22][N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)[N:5]2[C:10]=1[C:9]([NH2:11])=[N:8][CH:7]=[N:6]2.[Cl:28][C:29]1[CH:30]=[C:31]([CH:44]=[CH:45][CH:46]=1)[O:32][C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][C:34]=1[O:42][CH3:43].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.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>[Cl:28][C:29]1[CH:30]=[C:31]([CH:44]=[CH:45][CH:46]=1)[O:32][C:33]1[CH:38]=[CH:37][C:36]([C:2]2[C:3]([CH2:20][CH2:21][CH2:22][N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[C:4]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=3)[N:5]3[C:10]=2[C:9]([NH2:11])=[N:8][CH:7]=[N:6]3)=[CH:35][C:34]=1[O:42][CH3:43]To a solution of the compound (43 mg, 0.01 mmol) prepared in Example 15, the compound (29.4 mg, 0.15 mmol) prepared in Example 10, potassium phosphate (2N, 0.1 mL, 0.2 mmol), Pd(PPh3)4 (3 mg, 0.003 mmol) in DMF (3 mL) was deoxygenated by nitrogen gas for 5 minutes, and the reactor was sealed, heated at 90° C. for 6 hours. The mixture was concentrated, purified by prep TLC using 5% methanol in DCM (with 3% ammonium hydroxide solution) to give crude product which was further purified by prep HPLC to obtain the title compound (2.4 mg) having the following physical data.
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