Br[C:2]1[N:3]=[C:4]2[C:10]([C:11]([NH:13]C(C)(C)CO)=[O:12])=[CH:9][N:8](COCC[Si](C)(C)C)[C:5]2=[N:6][CH:7]=1.[I-].[Na+].CN[C@@H]1CCCC[C@H]1NC.ClC1C=C2C(C=NN2)=CC=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.[Cu]I>[N:3]1[CH:2]=[CH:7][N:6]=[C:5]2[NH:8][CH:9]=[C:10]([C:11]([NH2:13])=[O:12])[C:4]=12To a stirred solution of 2-bromo-N-(1-hydroxy-2-methylpropan-2-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (140 mg, 316 μmol) in toluene (2 mL) was added copper (I) iodide (3.17 mg, 35.4 μmol), sodium iodide (94.7 mg, 631 mmol) and trans-N,N′-dimethylcyclohexane-1,2-diamine (11.5 mg, 80.5 μmol). The reaction mixture was sealed under nitrogen and the mixture heated at 110° C. for 15 h. 6-Chloro-1H-indazole (48.2 mg, 316 μmol) and potassium phosphate tribasic (141 mg, 663 μmol) were added and the mixture degassed and filled with nitrogen, then heated in a sealed tube at 110° C. for 15 h. The mixture was filtered, the cake washed with ethyl acetate, and the filtrate concentrated in vacuo. Purification by chromatography (silica, 24 g Analogix column, 0-40% ethyl acetate in hexanes) gave 2-(6-chloro-1H-indazol-1-yl)-N-(1-hydroxy-2-methylpropan-2-yl)-5-(2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (124 mg, 76%). 1H NMR (CDCl3) δ: 9.14 (s, 1H), 8.51-8.55 (m, 1H), 8.38 (s, 1H), 8.26 (d, J=1.0 Hz, 1H), 7.91 (s, 1H), 7.78 (dd, J=8.5, 0.5 Hz, 1H), 7.33 (dd, J=8.5, 1.8 Hz, 1H), 5.73 (s, 2H), 3.80 (s, 2H), 3.57-3.64 (m, 2H), 1.56 (s, 6H), 0.96 (dd, J=8.8, 7.8 Hz, 2H), −0.02 (s, 9H).
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