反应详情

温度

100 °C

A solution of 3-chloro-2,5-diethylpyrazine (171 mg, 1.0 mmol), (1R,2S)-(+)-cis-1-amino-2-indanol (298 mg, 2.0 mmol), tris(dibenzylideneacetone)dipalladium (0) (28 mg, 0.03 mmol), and 2-(di-tertbutylphosphino)biphenyl (18 mg, 0.06 mmol) in toluene (2.0 mL) was purged with nitrogen and treated with sodium tertbutoxide (135 mg, 1.4 mmol). The resulting brown suspension was heated to 100° C. for 2 hours. At this time, the reaction was quenched with a saturated water solution of NaHCO3 and extracted twice with ethyl acetate (20 mL). The combined organics were washed with brine (15 mL), dried over MgSO4, filtered, and concentrated to give a black solid. This material was purified by biotage MPLC (40 g column, 25% ethyl acetate/heptane) to afford 184 mg (65%) of the title compound as a light purple solid. IR (diffuse reflectance) 3435, 3241, 2962, 2935, 2912, 2873, 1581, 1547, 1500, 1453, 1184, 1163, 1047, 744, 733 cm−1; OAMS supporting ions at: ESI+ 384.0; MS (CI) m/z 284 (MH+); HRMS (FAB) calcd for C17H21N3O+H1 284.1763, found 284.1754. [α]25D=12 (c 0.55, methylene chloride); Anal. Calcd for C17H21N3O: C, 72.06; H, 7.47; N, 14.83. Found: C, 72.15; H, 7.53; N, 14.42.

1. customAt this time, the reaction was quenched with a saturated water solution of NaHCO3
2. extractionextracted twice with ethyl acetate (20 mL)
3. washThe combined organics were washed with brine (15 mL)
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated
7. customto give a black solid
8. customThis material was purified by biotage MPLC (40 g column, 25% ethyl acetate/heptane)