反应详情

温度

85 °C

Charge a Kimble vial with methyl 3-bromo-6-{[(1R,2S)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]amino}pyrazine-2-carboxylate (0.45 g, 1.14 mmol), Pd(PPh3)4 (198 mg, 0.17 mmol), and 2,4-dichlorophenylboronic acid (325 mg, 1.71 mmol). Flush with N2 and add DMF (4 mL) and 2 M Na2CO3 (1.1 mL). The resulting mixture was heated at 85° C. overnight. The mixture was diluted with sat. aq. NaHCO3. Extract with Et2O. The organic extract was dried over MgSO4, filtered and concentrated. Purify by biotage MPLC (90 g column, 30% ethyl acetate/hexanes) to afford 290 mg (59%) of methyl 3-(2,4-dichlorophenyl)-6-{[(1R,2S)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]amino}pyrazine-2-carboxylate as a solid: 1H NMR (CDCl3) δ 3.06–3.09, 3.27–3.32, 3.80, 4.09–4.15, 4.84, 5.58, 7.28–7.49, 8.25; MS (ESI+) for C21H17Cl2N3O3 m/z 430 (M+H)+.

1. customFlush with N2
2. additionadd DMF (4 mL) and 2 M Na2CO3 (1.1 mL)
3. additionThe mixture was diluted with sat. aq. NaHCO3
4. extractionExtract with Et2O
5. extractionThe organic extract
6. dry with materialwas dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated
9. customPurify by biotage MPLC (90 g column, 30% ethyl acetate/hexanes)