Cl[C:2]1[N:7]=[C:6]([C:8]2[C:9]([N:28]([CH3:33])[S:29]([CH3:32])(=[O:31])=[O:30])=[CH:10][C:11]3[O:15][C:14]([C:16]4[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=4)=[C:13]([C:23]([NH:25][CH3:26])=[O:24])[C:12]=3[CH:27]=2)[CH:5]=[CH:4][C:3]=1[C:34]1([CH2:37]O)[CH2:36][CH2:35]1.[F:39][C:40]1[CH:48]=[CH:47][CH:46]=[C:45]2[C:41]=1[CH:42]=[C:43](B1OC(C)(C)C(C)(C)O1)[NH:44]2.C([O-])([O-])=O.[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCOCC1.O>[F:39][C:40]1[C:41]2[CH:42]=[C:43]3[C:2]4[N:7]=[C:6]([C:8]5[C:9]([N:28]([CH3:33])[S:29]([CH3:32])(=[O:30])=[O:31])=[CH:10][C:11]6[O:15][C:14]([C:16]7[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=7)=[C:13]([C:23]([NH:25][CH3:26])=[O:24])[C:12]=6[CH:27]=5)[CH:5]=[CH:4][C:3]=4[C:34]4([CH2:35][CH2:36]4)[CH2:37][N:44]3[C:45]=2[CH:46]=[CH:47][CH:48]=1To a solution of 5-(6-chloro-5-(1-(hydroxymethyl)cyclopropyl)pyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (80 mg, 0.143 mmol) and 4-fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (56.1 mg, 0.215 mmol) in 1,4-Dioxane (2 mL) and water (20 μL) was added Cs2CO3 (93 mg, 0.287 mmol) and DTBPF PdCl2 (21 mg, 0.032 mmol). The mixture was heated to 80° C., stirred overnight, concentrated in vacuo and dried. The residue was dissolved in DCM (2.00 mL), followed by addition of triphenylphosphine (94 mg, 0.358 mmol) and DIAD (0.070 mL, 0.358 mmol). The mixture was stirred at RT for 4 h. Preparative TLC (eluted with 20% ethyl acetate in DCM) gave 5-(11′-fluoro-6′H-spiro[cyclopropane-1,5′-indolo[1,2-h][1,7]naphthyridin]-2′-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (4.5 mg, yield: 5%) MS (M+H)+: 639.
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