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C. (4-Bromo-3-fluoro-phenyl)-(l-pyrimidin-2-yl-piperidin-4-yl)- amine: To the mixture of bromoaniline (1.5 mmol) and ketone (266 mg, 1.5 mmol) in MeOH/ AcOH(10:1, 5 ml) was added BH3-Py in THF (8M, 188 mul). The mixture was stirred at rt for 2h. The reaction mixture was concentrated and to the residue was added HCl (10%, 10 ml). The resulting mixture was stirred at rt for 30 min., then with cooling, the mixture was adjusted to alkaline with solid Na2CO3 and water. The aq. layer was extracted with EtOAc (5x 30 ml). The EtOAc was dried (Na2SO4) and concentrated. The residue was subjected to ISCO to give the titled compound as a white solid (150 mg).
Example 399Methyl 3-(4-bromo-3-fluorophenylamino)-2-(cyclopropanecarbonyl)acrylateA stirred mixture of <strong>[32249-35-7]methyl 3-cyclopropyl-3-oxopropanoate</strong> (3.49 g, 26.3 mmol), triethyl orthoformate (5.2 mL, 31.6 mmol), and 4-bromo-3-fluoroaniline (4.47 g, 26.0 mmol) was heated at 140 C overnight with a Dean Stark trap. After this time the reaction was cooled to room temperature, diluted with methylene chloride and filtered through a pad of silica. The filtrate was concentrated to afford the desired product (7.5 g, 85%) as a light yellow solid: ESI MS m/z 343 [C|4H13BrFN03 + H]+.
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 100℃; for 48h;Inert atmosphere;
To a solution of 4-bromo-3-fluoroaniline (474 mg, 2.51 mmol) in 1,4-dioxane (10 mL) was added Pd(dppf)Cl2 (183 mg, 0.25 mmol) and 2-(tributylstannyl)-l,3-oxazole (900 mg, 2.52 mmol). The resulting mixture was stirred for 48 h at 100 C and then cooled to room temperature. The reaction mixture was poured into water (10 mL) and then extracted with ethyl acetate (3 x 10 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The resulting crude product was purified by silica gel chromatography (eluting with 0: 100 to 50:50 ethyl acetate/petroleum ether) to afford 3-fluoro-4-(l,3-oxazol-2-yl)aniline (180 mg, 41%). LCMS (ES, m/z) 179 [M+H]+.
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