Synthetic method of carbazole and derivatives thereof
A synthesis method and derivative technology, applied in the direction of organic chemistry, etc., can solve the problems of inability to meet the needs of diversity, single product, etc., and achieve the effects of high product yield, simple synthesis route, and strong practicability.
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Embodiment 1
[0039] Embodiment 1 synthetic compound (1-1)
[0040]
[0041] Add H to the 250mL reaction flask 2 O (50mL), THF (50mL), 3-indole formaldehyde (5mmol, 726mg), 3-bromopropene (10mmol, 1290mg), 1,4-dihydropyridinate (5mmol, 1176mg) and indium powder (7mmol, 803 mg). The reaction mixture was reacted at 50° C. for 24 hours, and the reaction was complete as detected by TLC. Post-processing purification: the reaction mixture was extracted with EA (20 mL×2), and the organic phases were combined and washed with saturated NaCl (20 mL×1). After liquid separation, dry with anhydrous magnesium sulfate, remove the organic solvent under reduced pressure, separate and purify with silica gel column chromatography [V (petroleum ether): V (ethyl acetate) = 15:1] to obtain a pure product, light yellow Liquid, yield: 75%.
[0042] Compound (1-1) was detected:
[0043] 1 H NMR (400MHz, CDCl 3 ):δ7.93(s,1H),7.65(dd,J=7.9Hz,J=1.0Hz,1H),7.39(dt,J=8.1Hz,J=0.8Hz,1H)7.25-7.19(m, 1H), 7.17-7.1...
Embodiment 2
[0045] Embodiment 2 synthetic compound (1-2)
[0046]
[0047] Compound (1-1) (5 mmol, 856 mg), DMF (10 mL) and NaH (5 mmol, 240 mg) were added to a 25 mL two-necked flask. The reaction mixture was stirred at 0° C. for 10 minutes, and then 2-chloropyrimidine (6 mmol, 687 mg) was added, then raised to room temperature and reacted at 130° C., and the reaction was complete as detected by TLC. Post-treatment purification: add water (20 mL) to quench, extract with EA (20 mL×3), combine organic phases, and wash with saturated NaCl (20 mL×2). After liquid separation, dry with anhydrous magnesium sulfate, remove the organic solvent under reduced pressure, and separate and purify with silica gel column chromatography [V (petroleum ether): V (ethyl acetate) = 8:1] to obtain a pure product, colorless Liquid, yield: 80%.
[0048] Compound (1-2) is tested:
[0049] 1 H NMR (400MHz, CDCl 3 )δ8.78(d, J=8.3Hz, 1H), 8.65(d, J=4.8Hz, 2H), 8.05(s, 1H), 7.58(d, J=7.8Hz, 1H), 7.37-7.31( m...
Embodiment 3
[0053] Embodiment 3 synthetic compound (1-3)
[0054]
[0055] In a 10 mL Schlenk tube, add compound (1-2) (0.2 mmol, 49.86 mg), silver acetate (0.3 mmol, 50.1 mg), potassium trifluorovinyl borate (0.3 mmol, 40.2 mg), [RhCp*Cl 2 ] 2 (1mol%, 1.24mg), methanol (1mL), TFE (1mL) and air balloon (1L). The reaction mixture was reacted at 40° C. and detected by TLC until the reaction was complete. Carry out post-processing purification: remove the organic solvent under reduced pressure, separate and purify with silica gel column chromatography [V (petroleum ether): V (ethyl acetate) = 8: 1] to obtain a pure product, a colorless liquid, and the yield: 85%.
[0056] Compound (1-3) was detected:
[0057] 1 H NMR (400MHz, CDCl 3 )δ8.77(d, J=4.8Hz, 2H), 8.25(d, J=8.4Hz, 1H), 7.63-7.56(m, 1H), 7.32-7.19(m, 2H), 7.12-7.07(m ,1H),6.99(dd,J=17.4,11.9Hz,1H),5.98(dt,J=16.9,10.2,6.6Hz,1H),5.43(s,1H),5.41-5.37(m,1H), 5.15-5.09(m,1H),5.05-4.99(m,1H),2.98(dd,J=8.4,7.6Hz,2H),2.47(dd,J=7.8...
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