反应详情

温度

120 °C

A round bottom flask fitted with reflux condenser containing 2-methyl-2,3,4,9-tetrahydro-1H-b-carboline (16) (0.30 g, 1.62 mmol) and potassium tert-butoxide (0.22 g, 1.92 mmol) was vacuum purged and filled with argon, followed by addition of DMSO (5 mL). After stirring at 120° C. for 20 min, 4-bromomethyl-benzoic acid methyl ester (0.37 g, 1.62 mmol) was added and the mixture was stirred at 120° C. for 3 h. The reaction was quenched by addition of water (30 mL), transferred to a separatory funnel and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine (2×20 mL), dried (Na2SO4) and concentrated. The product was purified by MPCC (0 to 5% gradient of MeOH in CH2Cl2), which gave 180 mg (33%) of the title compound. 1H NMR (400 MHz, CDCl3): δ 7.95 (d, 2H, J=8.2 Hz), 7.54 (m, 1H, J=7.6 Hz), 7.18-7.11 (m, 4H), 7.15 (d, 2H, J=8.1 Hz), 5.25 (s, 2H), 3.89 (s, 3H), 3.53 (s, 2H), 2.90 (m, 2H), 2.80 (m, 2H), 2.51 (s, 3H). 13C NMR (100 MHz, CDCl3): δ 166.5, 141.9, 137.4, 130.4, 126.0, 122.8, 120.2, 118.6, 109.4, 106.7, 52.2, 51.3, 49.7, 46.6, 45.56, 42.1, 18.5. ESI-HRMS (m/z): [M+H]+ calcd. for C21H22N2O2, 335.1727. found, 335.1724.

1. customA round bottom flask fitted
2. temperaturewith reflux condenser
3. custompurged
4. additionfilled with argon
5. additionfollowed by addition of DMSO (5 mL)
6. stirringthe mixture was stirred at 120° C. for 3 h
7. customThe reaction was quenched by addition of water (30 mL)
8. customtransferred to a separatory funnel
9. extractionextracted with ethyl acetate (3×20 mL)
10. washThe combined organic layers were washed with brine (2×20 mL)
11. dry with materialdried (Na2SO4)
12. concentrationconcentrated
13. customThe product was purified by MPCC (0 to 5% gradient of MeOH in CH2Cl2), which