Synthesis method for biaryl benzimidazole compounds
The technology of a benzimidazole and a synthesis method is applied in the field of synthesis of biaryl benzimidazole compounds, can solve the problems of complicated preparation, low reaction yield and the like, and achieves the effects of simple operation, high yield and wide range of cheapness
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Embodiment 1
[0028] Preparation of biaryl benzimidazole compound (1): Under nitrogen protection, add 1.0mmol o-phenylenediamine, 1.0mmol p-bromobenzyl alcohol, 1.0mmol phenylboronic acid, 0.03mmol Pd / C , 2.0 mmol of ammonium bicarbonate, and 5 ml of water, the reaction tube was replaced with nitrogen for 3 times, then heated to 100° C. in an oil bath under magnetic stirring, and the reaction was refluxed for 6 hours. The oil bath was removed and lowered to room temperature; the Pd / C catalyst was recovered by filtration; the filtrate was concentrated by a rotary evaporator, and the concentrated solid was recrystallized with ethanol as a solvent to obtain pure product 1 with a yield of 87%. The NMR analysis data of this product are as follows: 1HNMR.(400MHz,DMSO-d6):13.09(br,1H),7.63(d,2H),7.10(d,3H),6.95(d,3H),6.65(d, 2H), 6.57(d, 2H), 1.77(s, 3H).
Embodiment 2
[0030] Preparation of Biarylbenzimidazole Compounds (4) : Under nitrogen protection, add 1.0mmol 4-methyl-1,2-o-phenylenediamine, 2.0mmol p-iodobenzyl alcohol, 2.0 Mmol p-methoxyphenylboronic acid, 0.05mmol Pd / C, 3.0mmol potassium bicarbonate, and 5ml water were used to replace the reaction tube with nitrogen for 3 times, then heated to 80°C with an oil bath under magnetic stirring, and the reaction was refluxed for 12 hours. The oil bath was removed and lowered to room temperature; the Pd / C catalyst was recovered by filtration; the filtrate was concentrated by a rotary evaporator, and the concentrated solid was recrystallized with ethanol as a solvent to obtain pure product 4 with a yield of 92%. The NMR analysis data of this product are as follows: 1HNMR.(400MHz,DMSO-d6):13.08(br,1H),8.11(d,2H),7.61(d,2H),7.53(d,2H),7.55-7.32( m,2H), 7.08(d,1H), 6.96(d,2H), 3.84(s,3H), 2.46(s,3H).
Embodiment 3
[0032] Preparation of Biarylbenzimidazoles (6): Under nitrogen protection, add 1.0mmol 4-methyl-1,2-o-phenylenediamine, 1.5mmol p-bromobenzyl alcohol, 2.5mmol P-cyanophenylboronic acid, 0.08mmol Pd / C, 4.0mmol sodium bicarbonate, and 5ml water were used to replace the reaction tube with nitrogen for 3 times, then heated to 90°C with an oil bath under magnetic stirring, and the reaction was refluxed for 6 hours. Remove the oil bath and drop to room temperature; filter and recover the Pd / C catalyst; the filtrate is concentrated with a rotary evaporator, and the concentrated solid is recrystallized with ethanol as a solvent to obtain the pure product 6 , 85% yield. The nuclear magnetic analysis data of this product are as follows: 1 HNMR.(400MHz, DMSO-d 6 ):d13.09(br,1H),8.17(d,2H),7.73(d,2H),7.68(d,2H),7.65(d,2H),7.60-7.50(m,1H),7.47- 7.37 (m, 1H), 7.11 (d, 1H), 2.47 (s, 3H).
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