10% |
With [2-(di-tert-butylphosphino)-2?,4?,6?-triisopropyl-1,1?-biphenyl][2-((2-aminoethyl)phenyl)]palladium(II) chloride; sodium t-butanolate; In 1,4-dioxane; for 20.0h;Sealed tube; Inert atmosphere; |
[00289] Sodium t-butoxide (101 mg, 1.05 mmol) was added to a solution of 2- bromo-5-phenyl-oxazole (72 mg, 0.32 mmol) and 3-methyl-5-morpholino-aniline (63 mg, 0.33mmol) in dry 1,4-dioxane (2 mL) at room temperature. The mixture was purged with nitrogen for 3 minutes. Chloro(2-di-t-butylphosphino-2',4',6'-tri-i-propyl- l,r-biphenyl)[2-(2-aminoethyl)phenyl] palladium(II) (/-BuXPhos Palladacycle) (8 mg, 0.01 mmol) was added and after purging with nitrogen for two more minutes, the vial was sealed and heated at 60 C for 20 hours. The reaction was cooled, diluted with pH7 buffer and water, then extracted with ethyl acetate. The organic layer was washed with brine, filtered through a plug of Florisil, dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel (12 g column; 10-60% ethyl acetate/dichloromethane) to afford the desired product. The above product was further triturated twice with ether to give N-(3- methyl-5-mo holinophenyl)-5-phenyl-oxazol-2-amine (11 mg, 10%) as a colorless solid. lH NMR (300 MHz, CDC13) delta 7.60-7.51 (m, 2H), 7.45 - 7.36 (m, 2H), 7.32- 7.23 (m, 1H), 7.17 (s, 1H), 7.06 (d, J = 2.1 Hz, 2H), 6.78 (s, 1H), 6.46 (t, J = 1.7 Hz, 1H), 3.94 - 3.85 (m, 4H), 3.26 - 3.17 (m, 4H), 2.36 (s, 3H) ppm. ESI-MS m/z calc. 335.1, found 336.1 (M+l)+; Retention time: 0.75 minutes. |