I[C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[Br-].[CH:12]1([Zn+])[CH2:14][CH2:13]1.O1CCOCC1>Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1.CO>[CH:12]1([C:2]2[CH:3]=[C:4]3[CH:10]=[CH:9][NH:8][C:5]3=[N:6][CH:7]=2)[CH2:14][CH2:13]15-Iodo-1H-pyrrolo[2,3-b]pyridine (21, 0.343 g, 1.40 mmol), cyclopropylzinc bromide (22, 12.6 mL, 0.500 M in tetrahydrofuran, 6.32 mmol) and [1,3-bis(diphenylphosphino)propane]-nickel(II) chloride (76.2 mg, 0.14 mmol) and 5.37 mL of 1,4-dioxane were combined in a reaction vessel. The reaction was heated at 100° C. overnight, then methanol was added and the reaction was concentrated under vacuum. Ethyl acetate and water were added to the residue, then filtered through a bed of celite and the celite bed washed with ethyl acetate. The filtrate was separated and the aqueous layer extracted with ethyl acetate. The organic layers were combined and washed with brine, dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography, eluting with ethyl acetate and hexane. Appropriate fraction were combined and concentrated under vacuum to provide the desired compound. MS (ESI) [M+H+]+=159.0.
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