[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[N:10][CH:11]=[C:12](Br)[N:13]=2)[NH:8][C:7]=1[CH3:16])=[O:5])[CH3:2].[CH3:17][O:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26].C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([C:21]3[CH:22]=[C:23]([O:27][CH3:28])[C:24]([O:25][CH3:26])=[C:19]([O:18][CH3:17])[CH:20]=3)[N:13]=2)[NH:8][C:7]=1[CH3:16])=[O:5])[CH3:2]To a flask charged with 2-Bromo-6-methyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ethyl ester (360 mg, 1.26 mmol), 3,4,5-trimethoxyphenylboronic acid (320 mg, 1.51 mMol), Pd(dppf)Cl2 (31 mg, 0.038 mmol) was added K2CO3 (520 mg, 3.75 mmol). The mixture was heated to 100° C. overnight. The reaction mixture was cooled, diluted with EtOAc and filtered over celite. The solution was washed with water and brine, dried over Na2SO4, filtered, and concentrated. Flash chromatography afforded 105 mg of 6-Methyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ethyl ester.
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