Br[CH2:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][O:22][CH3:23])=[CH:16][CH:15]=2)=[CH:6]1.C([SnH](CCCC)CCCC)CCC.CC(N=NC(C#N)(C)C)(C#N)C.O>C1(C)C=CC=CC=1>[CH3:23][O:22][CH2:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:7]2[C:8]3[N:9]=[CH:10][CH:11]=[CH:12][C:13]=3[N:5]3[C:6]=2[CH2:2][CH2:3][CH2:4]3)=[CH:15][CH:16]=1A solution of 1-(3-bromopropyl)-3-[4-(methoxymethoxy)phenyl]-1H-pyrrolo[3,2-b]pyridine (486 mg), tri-n-butyltin hydride (0.697 mL), and AIBN (21.27 mg) in toluene (25 mL) was heated at 110° C. overnight. To the mixture was added AIBN (21.27 mg), and the mixture was heated at 110° C. for 2 h. The mixture was added to water and extracted with AcOEt. The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (88 mg).
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