CN108383779B - 一种3′-芳基-2,2′-联吡啶-6-甲酰胺衍生物的制备方法 - Google Patents
一种3′-芳基-2,2′-联吡啶-6-甲酰胺衍生物的制备方法 Download PDFInfo
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Abstract
本发明公开了一种3′‑芳基‑2,2′‑联吡啶‑6‑甲酰胺衍生物的制备方法,该3′‑2,2′‑联吡啶‑6‑甲酰胺衍生物的结构式如下:
Description
技术领域
本发明属于有机合成技术领域,具体涉及一种3′-芳基-2,2′-联吡啶-6-甲酰胺衍生物的制备方法。
背景技术
2,2′-联吡啶由于具有强的给电子配位能力,常作为过渡金属的配体,与一系列的过渡金属离子生成金属配合物,这类配合物具有特殊的光、电和催化性质,具备广泛的应用价值。2,2′-联吡啶母核上C(SP2)-H官能团化是构建2,2′-联吡啶衍生物最直接的方法之一。然而,2,2′-联吡啶母核上直接C(SP2)-H官能团化反应却很少报道。2012年韩国的Sukbok Chang教授报道了一例铑催化的2,2′-联吡啶母核3,3′-位双烷基化反应(J.Am.Chem. Soc.2012,134,17778-17788)。其他过渡金属催化的2,2′-联吡啶母核直接C(SP2)-H官能团化反应还未见文献报道。主要原因在于,2,2′-联吡啶作为双齿配体极易与过渡金属形成稳定的配合物,从而阻止了过渡金属进一步活化C(SP2)-H键。因此,开发钯催化的2,2′-联吡啶C(SP2)-H官能团化的制备3′-芳基2,2′-联吡啶酰胺衍生物很有研究价值。
发明内容
本发明的目的在于提供一种3′-芳基-2,2′-联吡啶-6-甲酰胺衍生物的制备方法。
本发明的技术方案如下:
一种3′-芳基-2,2′-联吡啶-6-甲酰胺衍生物的制备方法,该3′-2,2′-联吡啶-6-甲酰胺衍生物的结构式如下:
该制备方法是在氮气气氛下,通过2,2′-联吡啶-6-甲酰胺衍生物、芳香碘代化合物、钯盐和有机溶剂于150~165℃反应24~48h而获得;
其中,R为直链烷基、异丙基、叔丁基、环己基、苯基;R1为氢、烷基、酰基、或烷氧基、卤素;R2为氢、卤素、烷基、酰基、酯基、氰基、硝基、氨基或烷氧基;R3为氢、卤素、烷基、酰基、氰基、酯基、氨基、硝基或烷氧基;R4为氢、卤素、烷基、酰基、酯基、氰基、硝基、氨基或烷氧基;R5为氢、烷基、酰基、烷氧基或卤素;
具体反应方程式如下:
在本发明的一个优选实施方案中,所述钯盐为Pd(OAc)2。
在本发明的一个优选实施方案中,所述2,2′-联吡啶-6-甲酰胺衍生物与芳香碘代化合物的摩尔比为1∶3。
在本发明的一个优选实施方案中,所述芳香碘代化合物、钯盐及相应的碱摩尔比为 1∶3∶4。
在本发明的一个优选实施方案中,包括如下步骤:
(1)将所述2,2′-联吡啶-6-甲酰胺衍生物、芳香碘代化合物、钯盐和有机溶剂置于反应容器中,氮气气氛下,150~165℃反应24~48h,反应完成后加入适量水或氯化钠溶液终止反应;
(2)将步骤(1)所得的物料用水洗,二氯甲烷萃取,得有机相;
(3)将步骤(2)所得的有机相经干燥、过滤、浓缩和柱层析纯化,得到所述3′-芳基2,2′-联吡啶酰胺衍生物。
进一步优选的,所述有机溶剂为1,3,5-三甲苯。
更进一步优选的,每毫摩尔所述的2,2′-联吡啶-6-甲酰胺衍生物对应5mL有机溶剂
本发明的有益效果是:
1、本发明首次合成3′-芳基2,2′-联吡啶酰胺衍生物;
2、本发明的方法收率高,反应条件较温和,后处理简便。
具体实施方式
以下通过具体实施方式对本发明的技术方案进行进一步的说明和描述。
实施例1
N-丁基-3-苯基-2,2′-联吡啶-6-甲酰胺的制备
将N-丁基-2,2′-联吡啶-6-甲酰胺0.2mmol,碘苯0.6mmol,C82CO3 0.8mol,加入1.5mL 1,3,5-三甲苯,N2环境下,置于160℃的油浴中,反应24h;加入适量水或氯化钠溶液停止反应,冷却至室温。反应液盐水洗,二氯甲烷萃取3次,收集有机相。有机相用无水Mg2SO4干燥,过滤,浓缩,柱层析纯化得到53.6mg目标产物,收率为81%。该化合物的核磁表征如下:1H NMR(500MHz,CDCl3)δ8.73(dd,J=4.7,1.7Hz,1H),8.16(dd,J= 7.8,1.0Hz,1H),8.04(dd,J=7.7,1.0Hz,1H),7.91(t,J=7.8Hz,1H),7.78(dd,J=7.7,1.7 Hz,1H),7.43(dd,J=7.7,4.7Hz,1H),7.34-7.29(m,3H),7.20-7.17(m,2H),6.80(s,1H), 3.16(dd,J=13.6,7.0Hz,2H),1.44-1.38(m,2H),1.29(dd,J=15.3,7.3Hz,2H),0.93(t,J= 7.3Hz,3H);13C NMR(126MHz,CDCl3)δ163.9,155.9,153.9,148.4,148.2,141.0,139.3, 137.9,137.0,128.7,128.3,126.8,126.3,123.3,121.1,38.7,31.6,20.0,13.8.
实施例2
3-(3-溴苯基)-N-丁基-2,2′-联吡啶6-甲酰胺的制备
将N-丁基-2,2′-联吡啶-6-甲酰胺0.2mmol,间溴碘苯0.6mmol,CS2CO3 0.8mol,加入1.5mL 1,3,5-三甲苯,N2环境下,置于160℃的油浴中,反应24h;加入适量水或氯化钠溶液停止反应,冷却至室温。反应液水洗,二氯甲烷萃取3次,有机相用无水Mg2SO4干燥,过滤,浓缩,柱层析纯化得到55.2mg目标产物,收率为67.3%。该化合物的核磁表征如下:1H NMR(500MHz,CDCl3)δ8.74(dd,J=4.7,1.4Hz,1H),8.21(d,J=7.7Hz,1H),8.08(d, J=7.6Hz,1H),7.94(t,J=7.8Hz,1H),7.75(dd,J=7.7,1.4Hz,1H),7.50-7.42(m,3H), 7.13(t,J=7.8Hz,1H),6.99(d,J=7.7Hz,1H),6.85(s,1H),3.22(dd,J=13.9,6.9Hz,2H), 1.46(dd,J=14.7,7.1Hz,2H),1.32(dd,J=15.0,7.4Hz,2H),0.95(t,J=7.3Hz,3H);13C NMR(126MHz,CDCl3)δ163.77(s),155.5,153.7,148.7,148.3,143.2,139.2,138.1,135.4, 131.4,129.9,129.7,127.6,126.3,123.4,122.3,121.3,39.0,31.8,20.1,13.8.
实施例3
4-(6-(丁基氨基甲酰基)-2,2′-联吡啶-3)苯甲酸乙酯的制备
将N-丁基-2,2′-联吡啶-6-甲酰胺0.2mmol,对甲酸乙酯碘苯0.6mmol,CS2CO30.8mol,加入 1.5mL 1,3,5-三甲苯,N2环境下,置于160℃的油浴中,反应24h;加入适量水或氯化钠溶液停止反应,冷却至室温。反应液水洗,二氯甲烷萃取3次,有机相用无水Mg2SO4干燥,过滤,浓缩,柱层析纯化得到70.3mg目标产物,收率为87%。该化合物的核磁表征如下:1H NMR(500MHz,CDCl3)δ8.76(dd,J=4.7,1.6Hz,1H),8.23(dd,J=7.8,1.0Hz, 1H),8.06(dd,J=7.7,1.0Hz,1H),8.03-8.00(m,2H),7.94(t,J=7.8Hz,1H),7.78(dd,J= 7.7,1.6Hz,1H),7.48-7.45(m,1H),7.27(dd,J=6.6,1.8Hz,2H),6.71(t,J=5.5Hz,1H),4.41-4.37(m,2H),3.13-3.09(m,2H),1.41(d,J=7.1Hz,3H),1.36-1.32(m,2H),1.29- 1.25(m,2H),0.92(t,J=7.3Hz,3H);13C NMR(126MHz,CDCl3)δ166.0,163.7,155.5, 153.8,148.7,148.3,145.8,139.1,138.2,136.1,129.6,129.0,128.7,126.3,123.4,121.4,61.1, 38.7,31.6,20.0,14.3,13.7.
实施例4
N-丁基-3-(3-氯苯基)-2,2′-联吡啶-6-甲酰胺的制备
将N-丁基-2,2′-联吡啶-6-甲酰胺0.2mmol,间氯碘苯0.6mmol,CS2CO3 0.8mol,加入1.5mL 1,3,5-三甲苯,N2环境下,置于160℃的油浴中,反应24h;加入适量水或氯化钠溶液停止反应,冷却至室温。反应液水洗,二氯甲烷萃取3次,有机相用无水Mg2SO4干燥,过滤,浓缩,柱层析纯化得到64.6mg目标产物,收率为88.5%。该化合物的核磁表征如下:1H NMR(500MHz,CDCl3)68.78(dd,J=4.7,1.6Hz,1H),8.23(d,J=7.8Hz,1H),8.11(d, J=7.7Hz,1H),7.97(t,J=7.8Hz,1H),7.79(dd,J=7.7,1.6Hz,1H),7.48(dd,J=7.7,4.7 Hz,1H),7.36-7.31(m,2H),7.23(t,J=7.8Hz,1H),6.98(d,J=7.7Hz,1H),6.90(s,1H), 3.25(dd,J=13.9,6.9Hz,2H),1.47(dd,J=8.6,6.3Hz,2H),1.38-1.33(m,2H),0.97(t,J= 7.3Hz,3H);13C NMR(126MHz,CDCl3)δ163.8,155.5,153.8,148.7,148.4,142.9,139.2, 138.1,135.6,134.3,129.4,128.6,127.1,127.0,126.3,123.4,121.3,39.0,31.7,20.1,13.8.
实施例5
N-丁基-3-(3-氟苯基)-2,2′-联吡啶-6-甲酰胺的制备
将N-丁基-2,2′-联吡啶-6-甲酰胺0.2mmol,间氟碘苯0.6mmol,CS2CO3 0.8mol,加入1.5mL 1,3,5-三甲苯,N2环境下,置于160℃的油浴中,反应24h;加入适量水或氯化钠溶液停止反应,冷却至室温。反应液水洗,二氯甲烷萃取3次,有机相用无水Mg2SO4干燥,过滤,浓缩,柱层析纯化得到54.4mg目标产物,收率为78%。该化合物的核磁表征如下:1H NMR(500MHz,CDCl3)δ8.76(dd,J=4.7,1.6Hz,1H),8.20(dd,J=7.8,0.9Hz,1H), 8.09(dd,J=7.7,0.9Hz,1H),7.95(t,J=7.8Hz,1H),7.78(dd,J=7.7,1.6Hz,1H),7.46(dd, J=7.7,4.7Hz,1H),7.30-7.26(m,1H),7.04-6.92(m,4H),3.23(dd,J=13.6,7.0Hz,2H), 1.47-1.42(m,2H),1.33(dd,J=15.2,7.3Hz,2H),0.96(t,J=7.3Hz,3H).13C NMR(126 MHz,CDCl3)δ163.74,162.5(d,J=246.9Hz),155.6,153.8,148.5,148.3,143.2(d,J=7.8 Hz),139.0,138.0,135.7(d,J=1.9Hz),129.7(d,J=8.3Hz),126.3,124.5(d,J=2.9Hz),123.3,121.2,115.6(d,J=21.9Hz),113.7(d,J=20.9Hz),38.8,31.5,20.0,13.7.
实施例6
3-(4-乙酰基苯基)-N-丁基-2,2′-联吡啶-6-甲酰胺的制备
将N-丁基-2,2′-联吡啶-6-甲酰胺0.2mmol,对碘苯乙酮0.6mmol,CS2CO3 0.8mol,加入1.5 mL 1,3,5-三甲苯,N2环境下,置于160℃的油浴中,反应48h;加入适量水或氯化钠溶液停止反应,冷却至室温。反应液水洗,二氯甲烷萃取3次,有机相用无水Mg2SO4干燥,过滤,浓缩,柱层析纯化得到56.1mg目标产物,收率为75.2%。该化合物的核磁表征如下:1HNMR(500MHz,CDCl3)68.77(dd,J=4.7,1.7Hz,1H),8.21(dd,J=7.8,1.1Hz,1H), 8.07(dd,J=7.7,1.1Hz,1H),7.94(dd,J=9.4,7.3Hz,3H),7.78(dd,J=7.7,1.7Hz,1H), 7.47(dd,J=7.8,4.7Hz,1H),7.31-7.29(m,2H),6.77(s,1H),3.11-3.07(m,2H),2.60(s, 3H),1.34-1.29(m,2H),1.28-1.23(m,2H),0.91(t,J=7.2Hz,3H);13C NMR(126MHz, CDCl3)δ197.1,163.7,155.5,153.8,148.8,148.4,146.0,139.1,138.2,135.9,135.4,129.0, 128.4,126.4,123.4,121.4,38.8,31.7,26.5,20.0,13.7.
实施例7
N-丁基-3-(4-硝基苯基)-2,2′-联吡啶-6-甲酰胺的制备
将N-丁基-2,2′-联吡啶-6-甲酰胺0.2mmol,对硝基碘苯0.6mmol,CS2CO3 0.8mol,加入1.5 mL 1,3,5-三甲苯,N2环境下,置于160℃的油浴中,反应24h;加入适量水或氯化钠溶液停止反应,冷却至室温。反应液水洗,二氯甲烷萃取3次,有机相用无水Mg2SO4干燥,过滤,浓缩,柱层析纯化得到60.8mg目标产物,收率为80.8%。该化合物的核磁表征如下:1HNMR(500MHz,CDCl3)δ8.81(dd,J=4.7,1.6Hz,1H),8.25(dd,J=7.8,1.0Hz,1H), 8.22-8.20(m,2H),8.11(dd,J=7.7,1.0Hz,1H),7.98(t,J=7.8Hz,1H),7.79(dd,J=7.8,1.6Hz,1H),7.51(dd,J=7.8,4.7Hz,1H),7.39-7.37(m,2H),6.75(s,1H),3.13(d,J=6.6Hz,2H),1.35-1.30(m,2H),1.28-1.23(m,2H),0.93(d,J=7.3Hz,3H);13C NMR(126 MHz,CDCl3)δ163.5,155.2,153.9,149.3,148.4,148.0,146.7,139.0,138.4,134.7,129.6,126.5,123.6,123.5,121.7,38.8,31.7,20.0,13.6.
实施例8
3-(4-溴苯基)-N-丁基-2,2′-联吡啶-6-甲酰胺的制备
将N-丁基-2,2′-联吡啶-6-甲酰胺0.2mmol,对溴碘苯0.6mmol,CS2CO3 0.8mol,加入1.5mL 1,3,5-三甲苯,N2环境下,置于160℃的油浴中,反应24h;加入适量水或氯化钠溶液停止反应,冷却至室温。反应液水洗,二氯甲烷萃取3次,有机相用无水Mg2SO4干燥,过滤,浓缩,柱层析纯化得到69.4mg目标产物,收率为87.6%。该化合物的核磁表征如下:1H NMR(500MHz,CDCl3)δ8.75-8.72(m,1H),8.20(d,J=7.7Hz,1H),8.08-8.05(m, 1H),7.93(dd,J=7.8,4.3Hz,1H),7.75-7.71(m,1H),7.47-7.41(m,3H),7.06(d,J=8.4 Hz,2H),6.81(s,1H),3.25-3.21(m,2H),1.46-1.41(m,2H),1.36-1.30(m,2H),0.97- 0.93(m,3H);13C NMR(126MHz,CDCl3)δ163.7,155.6,153.5,148.5,148.33(s),140.0, 139.1,138.1,135.7,131.4,130.3,126.3,123.4,121.3,121.1,38.9,31.7,20.1,13.8.
实施例9
N-丁基-5-氯-2,2′:3′,2″-三联吡啶-6-甲酰胺的制备
将N-丁基-2,2′-联吡啶-6-甲酰胺0.2mmol,5-氯-2-碘代吡啶0.6mmol,CS2CO30.8mol,加入 1.5mL 1,3,5-三甲苯,N2环境下,置于160℃的油浴中,反应24h;加入适量水或氯化钠溶液停止反应,冷却至室温。反应液水洗,二氯甲烷萃取3次,有机相用无水Mg2SO4干燥,过滤,浓缩,柱层析纯化得到50.0mg目标产物,收率为73.6%。该化合物的核磁表征如下:1H NMR(500MHz,CDCl3)δ8.37(d,J=2.4Hz,1H),8.25(d,J=7.8Hz,1H),8.14 (d,J=7.7Hz,1H),7.99(t,J=7.8Hz,1H),7.79(dd,J=7.8,1.6Hz,1H),7.52(dd,J=7.7, 4.7Hz,1H),7.38(dd,J=8.2,2.5Hz,1H),7.27(d,J=8.2Hz,1H),6.86(d,J=5.4Hz,1H), 3.30-3.26(m,2H),1.51-1.46(m,2H),1.37-1.30(m,2H),0.97(d,J=7.3Hz,3H);13C NMR(126MHz,CDCl3)δ163.5,155.2,154.0,150.2,149.3,148.9,148.4,149.3,139.1,138.8, 138.4,135.6,132.0,126.6,123.7,123.6,121.7,38.9,31.6,20.1,13.7.
实施例10
N-丁基-3-(4-甲酰基苯基)-2,2′-联吡啶-6-甲酰胺的制备
将N-丁基-2,2′-联吡啶-6-甲酰胺0.2mmol,对碘苯甲醛0.6mmol,CS2CO3 0.8mol,加入1.5 mL 1,3,5-三甲苯,N2环境下,置于160℃的油浴中,反应24h;加入适量水或氯化钠溶液停止反应,冷却至室温。反应液水洗,二氯甲烷萃取3次,有机相用无水Mg2SO4干燥,过滤,浓缩,柱层析纯化得到65.6mg目标产物,收率为91.3%。该化合物的核磁表征如下:
1H NMR(500MHz,CDCl3)δ10.03(s,1H),8.79(dd,J=4.7,1.5Hz,1H),8.24(dd,J=7.8, 0.9Hz,1H),8.08(d,J=7.7Hz,1H),7.97(d,J=7.8Hz,1H),7.87(d,J=8.1Hz,2H),7.81 (dd,J=7.7,1.5Hz,1H),7.49(dd,J=7.7,4.7Hz,1H),7.38(d,J=8.1Hz,2H),6.75(t,J= 5.5Hz,1H),3.12-3.08(m,2H),1.33(dd,J=9.2,5.7Hz,2H),1.27-1.22(m,2H),0.91(t,J =7.2Hz,3H);13C NMR(126MHz,CDCl3)δ191.2,163.6,155.3,153.7,148.9,148.3,147.4, 139.0,138.2,135.6,134.7,129.6,129.4,126.4,123.4,121.4,38.7,31.6,19.9,13.6.
本领域普通技术人员可知,本发明的技术方案在下述范围内变化时,仍然能够得到与上述实施例相同或相近的技术效果,仍然属于本发明的保护范围:
以上所述,仅为本发明的较佳实施例而已,故不能依此限定本发明实施的范围,即依本发明专利范围及说明书内容所作的等效变化与修饰,皆应仍属本发明涵盖的范围内。
Claims (5)
2.如权利要求1所述的制备方法,其特征在于:所述2,2′-联吡啶-6-甲酰胺衍生物与芳香碘代化合物的摩尔比为1:3。
3.如权利要求1所述的制备方法,其特征在于:所述芳香碘代化合物、Pd(OAc)2及CS2CO3摩尔比为1:3:4。
4.如权利要求1至3中任一权利要求所述的制备方法,其特征在于:包括如下步骤:
(1)将所述2,2′-联吡啶-6-甲酰胺衍生物、芳香碘代化合物、CS2CO3、Pd(OAc)2和1,3,5-三甲苯置于反应容器中,氮气气氛下,150~165℃反应24~48h,反应完成后加入适量水或氯化钠溶液终止反应;
(2)将步骤(1)所得的物料用水洗,二氯甲烷萃取,得有机相;
(3)将步骤(2)所得的有机相经干燥、过滤、浓缩和柱层析纯化,得到所述3′-芳基-2,2′-联吡啶-6-甲酰胺衍生物。
5.如权利要求4所述的制备方法,其特征在于:每毫摩尔所述的2,2′-联吡啶-6-甲酰胺衍生物对应5mL有机溶剂。
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