N-alkyl substituted indole-imidazolium salt compound and preparation method thereof
A technology of salt compounds and compounds, applied in organic chemistry, pharmaceutical formulations, drug combinations, etc.
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[0018] The preparation method specifically includes:
[0019] A, the preparation of compound N-alkyl substituted indole:
[0020] Using indole as raw material, synthesize N-alkyl substituted indole with dibromoalkane in anhydrous DMF solvent: dissolve indole in anhydrous DMF, add sodium hydroxide solid at 0 ℃, the amount is molar ratio For indole: sodium hydroxide = 1: 2, the dosage of anhydrous DMF is 20 ml: 1g indole, stir for 5 minutes, then add dibromoalkane (1,3-dibromopropane, 1,4- Dibromobutane or 1,5-dibromopentane) in anhydrous DMF, the molar ratio is dibromoalkane:indole=3:1, the amount of anhydrous DMF is 5 ml : 1 ml dibromoalkane , after stirring for 5 hours at room temperature, dilute with ethyl acetate (50 ml: 1g substrate), wash with water (50 ml) and saturated brine (50 ml) respectively, dry the organic phase with anhydrous Na2SO4, filter, and solvent After concentrating under reduced pressure, perform silica gel column chromatography with n-hexane as eluent ...
Embodiment 1
[0026] Preparation of Compound 5: See Preparation Methods A, B, and C above.
[0027]
[0028] Compound 5: Formula C 27 h 27 Br 2 N 3 , yield 69%. White solid, m.p. 108-109 o C. IR ν max (cm -1 ): 3446, 3129, 2361, 2052, 1611, 1562, 1445, 1384, 1312, 1268, 1222, 1129, 1069, 1024, 957, 860, 743, 616, 563, 428. 1 H NMR (400 MHz, DMSO): δ9.72 (1H, s), 7.75 (2H, s), 7.68 (1H, s), 7.55-7.53 (1H, d, J =7.37 Hz),7.49-7.47 (1H, d, J = 7.69 Hz), 7.41-7.35 (3H, m), 7.29-7.27 (1H, d, J = 6.73Hz), 7.12-7.09 (1H, t, J = 14.11 Hz), 7.03-7.00 (1H, t, J = 13.47 Hz), 6.43(1H, s), 5.71 (2H, s), 4.52 (2H, s), 4.36 (2H, s), 2.43 (2H, s), 2.35 (6H, s). 13 C NMR (100 MHz, DSMO): δ 141.82, 136.61, 136.54, 135.57, 133.26, 132.87,130.92, 130.37, 129.64, 129.56, 128.58, 128.47, 128.30, 128.16, 122.91,121.14, 120.55, 119.14, 113.34, 113.17, 109.87, 100.89, 50.20, 44.66, 42.80, 29.22, 20.08, 20.01.
Embodiment 2
[0030] Preparation of Compound 6: See Preparation Methods A, B, and C above.
[0031]
[0032] Compound 6: Molecular Formula C 27 h 28 BrN 3 , yield 63%. White solid, m.p. 164-165 o C. IR ν max (cm -1 ): 3448, 3128, 2320, 2051, 1644, 1561, 1456, 1354, 1262, 1128, 1069, 994,955, 861, 743, 614, 541. 1 H NMR (400 MHz, DMSO): δ 9.79 (1H, s), 9.48 (1H, s),7.71 (1H, s), 7.67 (1H, s), 7.55-7.53 (1H, d, J = 7.66 Hz), 7.48-7.46 (1H, d, J = 8.06 Hz), 7.41-7.40 (1H, d, J = 3.07 Hz), 7.39 (1H, s), 7.37 (1H, s), 7.21 (1H, s), 7.19 (1H, s), 7.13-7.09 (1H, m), 7.04-7.00 (1H, m) , 6.43-6.42(1H, d, J = 3.04 Hz), 5.59 (2H, s), 4.48-4.44 (2H, t, J = 14.76 Hz), 4.38-4.34 (2H, t, J = 13.75 Hz), 2.47-2.43 (2H, t, J= 14.29 Hz), 2.35 (3H, s), 2.34 (3H, s), 2.27 (3H, s). 13 C NMR (100 MHz, DSMO): δ 141.11, 138.04, 136.28,135.53, 131.07, 129.63, 129.44, 129.29, 128.45, 128.19, 128.13, 121.07,120.49, 119.07, 113.20, 113.08, 109.75, 100.87, 49.45, 44.51, 42.75, 29.01, 20.69, 19.99,...
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