反应详情

To a solution of the 2-isobutyl-N,N-bis(4-methoxybenzyl)imidazo[1,2-a]quinoxalin-4-amine (134 mg, 0.28 mmol) (Example 1, D) in 2 mL of tetrahydrofuran was added n-butyl lithium (2.5M, 0.2 mL, 0.50 mmol) at −78° C. After being stirred at that temperature for 1 hour, 1,2-epoxy-2-methylpropane (72 mg, 1.0 mmol) was added. The reaction mixture was stirred at −78° C. for 2 hours, and then at room temperature for 4 hours. The reaction was quenched with 10 mL of saturated aqueous ammonium chloride. The resulting mixture was extracted with 100 mL of ethyl acetate. The organic layer was separated and washed with water (20 mL), brine (20 mL), dried over MgSO4, filtered and concentrated. The crude product was purified by flash column chromatography eluted with ethyl acetate and hexanes to give the titled compound (35 mg, 19%) and recovered starting material (100 mg, 63%). MS: MH+=553. 1H NMR (300 MHz, CDCl3): δ 8.41 (dd, 1H), 7.67 (dd, 1H), 7.20-7.37 (m, 6H), 6.84 (m, 4H), 5.31 (brs, 4H), 3.79 (s, 6H), 3.51 (s, 2H), 2.58 (d, 2H), 2.14 (m, 1H), 1.37 (s, 6H), 0.88 (d, 6H).

1. stirringThe reaction mixture was stirred at −78° C. for 2 hours
2. waitat room temperature for 4 hours
3. customThe reaction was quenched with 10 mL of saturated aqueous ammonium chloride
4. extractionThe resulting mixture was extracted with 100 mL of ethyl acetate
5. customThe organic layer was separated
6. washwashed with water (20 mL), brine (20 mL)
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated
10. customThe crude product was purified by flash column chromatography
11. washeluted with ethyl acetate and hexanes