Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[N:15]=[CH:14][N:13]([C:16]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[N:12]=3)[CH:9]=2)[N:4]([CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][O:36]2)[N:3]=1.[C:41]1([C:47]2[CH:51]=[C:50]([CH2:52][N:53]3[CH2:58][CH2:57][CH:56]([CH2:59][NH2:60])[CH2:55][CH2:54]3)[O:49][N:48]=2)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1>[C:41]1([C:47]2[CH:51]=[C:50]([CH2:52][N:53]3[CH2:54][CH2:55][CH:56]([CH2:59][NH:60][C:2]4[C:10]5[C:5](=[CH:6][CH:7]=[C:8]([C:11]6[N:15]=[CH:14][N:13]([C:16]([C:29]7[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=7)([C:23]7[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=7)[C:17]7[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=7)[N:12]=6)[CH:9]=5)[N:4]([CH:35]5[CH2:40][CH2:39][CH2:38][CH2:37][O:36]5)[N:3]=4)[CH2:57][CH2:58]3)[O:49][N:48]=2)[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=13-Bromo-1-(tetrahydro-2H-pyran-2-yl)-5-(1-trityl-1H-1,2,4-triazol-3-yl)-1H-indazole (0.25 g, prepared according to the reported preparation in US 2004/0127536), the compound prepared in Example 9 (0.29 g), racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.040 g), and sodium tert-butoxide (0.20 g) were suspended in toluene (6 mL) and purged with argon. Tris(dibenzylideneacetone)dipalladium(0) (0.019 g) was added and the system was sealed and heated at 100° C. overnight. The reaction mixture was cooled to room temperature and partitioned between dichloromethane and a saturated aqueous sodium bicarbonate solution. The organics were dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel to obtain the title compound (0.13 g) having the following physical data.
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