Br[C:2]1[CH:3]=[N:4][N:5]([CH3:20])[C:6]=1[CH:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]1.[CH3:21][C:22]1[N:26]=[C:25]([C:27]2[N:28]=[C:29]3[N:39]([CH:40]=2)[CH2:38][CH2:37][O:36][C:35]2[C:30]3=[CH:31][CH:32]=[C:33](B(O)O)[CH:34]=2)[N:24]([CH:44]([CH3:46])[CH3:45])[N:23]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:16]([O:15]1[CH2:10][CH2:11][CH2:12][CH:7]([C:6]2[N:5]([CH3:20])[N:4]=[CH:3][C:2]=2[C:33]2[CH:34]=[C:35]3[C:30](=[CH:31][CH:32]=2)[C:29]2[N:39]([CH:40]=[C:27]([C:25]4[N:24]([CH:44]([CH3:45])[CH3:46])[N:23]=[C:22]([CH3:21])[N:26]=4)[N:28]=2)[CH2:38][CH2:37][O:36]3)[CH2:8][NH:9][C:13]1=[O:14])([CH3:19])([CH3:18])[CH3:17]To a solution of tert-butyl 3-(4-bromo-1-methyl-1H-pyrazol-5-yl)piperidine-1-carboxylate (680 mg, 1.98 mmol) in dioxane (20.0 mL), was added {4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaen-12-yl}boronic acid (660 mg, 1.87 mmol), K2CO3 (780 mg, 5.70 mmol), and Pd(dppf)Cl2 (117 mg, 0.19 mmol). The resulting mixture was stirred at 80° C. for 18 h. After concentration, the residue was diluted with EtOAc (20 mL) and washed with brine (20 mL). The organic layer was dried over Na2SO4, filtered, and concentrated. The crude product was purified by silica gel chromatography eluting with a 0-20% gradient of EtOAc in petroleum ether to give 1-tert-butyl-5-(1-methyl-4-{4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaen-12-yl}-1H-pyrazol-5-yl)-λ3,3-oxazocan-2-one (540 mg, 50% yield) as a yellow solid. LCMS (ESI) m/z: 573.4 [M+H+].
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