Br[C:2]1[C:3]([CH3:10])=[N:4][CH:5]=[C:6]([CH3:9])[C:7]=1[NH2:8].[C:11]([O:15][CH2:16][CH3:17])(=[O:14])[CH:12]=[CH2:13].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCN(CC)CC>CN(C=O)C.O.C(O[Pd]OC(=O)C)(=O)C>[NH2:8][C:7]1[C:6]([CH3:9])=[CH:5][N:4]=[C:3]([CH3:10])[C:2]=1/[CH:13]=[CH:12]/[C:11]([O:15][CH2:16][CH3:17])=[O:14]A mixture of 3-bromo-2,5-dimethylpyridin-4-amine (5.0 g, 25 mmol), ethyl acrylate (5.0 g, 50 mmol), diacetoxypalladium (1.12 g, 5.0 mmol), PPh3 (3.28 g, 12.5 mmol), and NEt3 (7.6 g, 75 mmol) in DMF (50 mL) was heated in a microwave reactor at 150° C. for 2 h. The reaction mixture was cooled, diluted with water (100 mL), and extracted with DCM (250 mL×3). The combined organic layers were washed with saturated sodium chloride solution (100 mL×3), dried with sodium sulfate, concentrated, and purified by column chromatography to give 5.0 g of the product as a yellow solid. MS (ESI): m/z 221.2 [M+H]+.
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