Cl[C:2]1[N:7]=[C:6]2[N:8]([CH3:14])[C:9](=[O:13])[C:10]([CH3:12])([CH3:11])[C:5]2=[CH:4][CH:3]=1.[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CC(C)([O-])C.[Na+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd]>[CH2:15]([NH:22][C:2]1[N:7]=[C:6]2[N:8]([CH3:14])[C:9](=[O:13])[C:10]([CH3:12])([CH3:11])[C:5]2=[CH:4][CH:3]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1To a mixture of 6-chloro-1,3,3-trimethyl-1H-pyrrolo[2,3-b]pyridin-2-one (500 mg, 2.37 mmol), benzylamine (763 mg, 778 μl, 7.12 mmol) and sodium tert-butoxide (388 mg, 4.03 mmol) in toluene (10 ml) were added tris(dibenzylideneacetone)dipalladium (0) chloroform adduct (49.1 mg, 47.5 μmol) and BINAP (29.6 mg, 47.5 μmol). The reaction mixture was heated to 115° C. and stirred for 48 hours. The reaction mixture was diluted with EtOAc, silica gel was added and the mixture concentrated in vacuo. The obtained material was purified silica gel chromatography using heptane/ethyl acetate as eluent. The title compound was obtained as light yellow solid (616 mg).
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