2-(3-(2-氨基-2-氧代乙酰基)-1-苄基-2-乙基-1H-吲哚-4-基氧基)乙酸叔丁酯合成路线 （共 16 条）
反应条件
1: in dichloromethane
T=20°C; 2 h;
2: With 1,1,1,3,3,3-hexamethyl-disilazane in dichloromethane
T=20°C; Further stages.;
参考文献
Sanz, Roberto; Castroviejo, M. Pilar; Guilarte, Veronica; Perez, Antonio; Fananas, Francisco J.
Journal of Organic Chemistry, 2007 , vol. 72, # 14 p. 5113 - 5118
反应条件
1.1: NaH / dimethylformamide / 0.08 h / 0 °C
1.2: 83 percent / dimethylformamide / 2 h
2.1: 68 percent / H2 / Pd/C / methanol / 2 h / 2068.59 Torr
3.1: NaH / dimethylformamide / 0.08 h / 20 °C
3.2: 87 percent / dimethylformamide / 0.5 h
4.1: CH2Cl2 / 2 h / 20 °C
5.1: 0.505 g / NH3 / CH2Cl2 / 0.17 h / 20 °C
View Scheme
参考文献
Smart, Brian P.; Oslund, Rob C.; Walsh, Laura A.; Gelb, Michael H.
Journal of Medicinal Chemistry, 2006 , vol. 49, # 10 p. 2858 - 2860
反应条件
1.1: 77 percent / NaBH4; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C
2.1: NaH / dimethylformamide / 0.08 h / 0 °C
2.2: 83 percent / dimethylformamide / 2 h
3.1: 68 percent / H2 / Pd/C / methanol / 2 h / 2068.59 Torr
4.1: NaH / dimethylformamide / 0.08 h / 20 °C
4.2: 87 percent / dimethylformamide / 0.5 h
5.1: CH2Cl2 / 2 h / 20 °C
6.1: 0.505 g / NH3 / CH2Cl2 / 0.17 h / 20 °C
View Scheme
参考文献
Smart, Brian P.; Oslund, Rob C.; Walsh, Laura A.; Gelb, Michael H.
Journal of Medicinal Chemistry, 2006 , vol. 49, # 10 p. 2858 - 2860
反应条件
1.1: 68 percent / H2 / Pd/C / methanol / 2 h / 2068.59 Torr
2.1: NaH / dimethylformamide / 0.08 h / 20 °C
2.2: 87 percent / dimethylformamide / 0.5 h
3.1: CH2Cl2 / 2 h / 20 °C
4.1: 0.505 g / NH3 / CH2Cl2 / 0.17 h / 20 °C
View Scheme
参考文献
Smart, Brian P.; Oslund, Rob C.; Walsh, Laura A.; Gelb, Michael H.
Journal of Medicinal Chemistry, 2006 , vol. 49, # 10 p. 2858 - 2860
反应条件
1.1: 62 percent / lithium aluminum hydride / tetrahydrofuran / 12 h / Heating
2.1: 77 percent / NaBH4; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C
3.1: NaH / dimethylformamide / 0.08 h / 0 °C
3.2: 83 percent / dimethylformamide / 2 h
4.1: 68 percent / H2 / Pd/C / methanol / 2 h / 2068.59 Torr
5.1: NaH / dimethylformamide / 0.08 h / 20 °C
5.2: 87 percent / dimethylformamide / 0.5 h
6.1: CH2Cl2 / 2 h / 20 °C
7.1: 0.505 g / NH3 / CH2Cl2 / 0.17 h / 20 °C
View Scheme
参考文献
Smart, Brian P.; Oslund, Rob C.; Walsh, Laura A.; Gelb, Michael H.
Journal of Medicinal Chemistry, 2006 , vol. 49, # 10 p. 2858 - 2860
反应条件
1.1: 94 percent / K2CO3 / acetone / 72 h / Heating
2.1: NaH / dimethylformamide / 0.08 h / 0 °C
2.2: 80 percent / dimethylformamide / 0.5 h / 20 °C
3.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 - 20 °C
3.2: 89 percent / hexane; tetrahydrofuran / 12.5 h / -78 - 20 °C
4.1: 62 percent / lithium aluminum hydride / tetrahydrofuran / 12 h / Heating
5.1: 77 percent / NaBH4; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C
6.1: NaH / dimethylformamide / 0.08 h / 0 °C
6.2: 83 percent / dimethylformamide / 2 h
7.1: 68 percent / H2 / Pd/C / methanol / 2 h / 2068.59 Torr
8.1: NaH / dimethylformamide / 0.08 h / 20 °C
8.2: 87 percent / dimethylformamide / 0.5 h
9.1: CH2Cl2 / 2 h / 20 °C
10.1: 0.505 g / NH3 / CH2Cl2 / 0.17 h / 20 °C
View Scheme
参考文献
Smart, Brian P.; Oslund, Rob C.; Walsh, Laura A.; Gelb, Michael H.
Journal of Medicinal Chemistry, 2006 , vol. 49, # 10 p. 2858 - 2860
反应条件
1.1: NaH / dimethylformamide / 0.08 h / 0 °C
1.2: 80 percent / dimethylformamide / 0.5 h / 20 °C
2.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 - 20 °C
2.2: 89 percent / hexane; tetrahydrofuran / 12.5 h / -78 - 20 °C
3.1: 62 percent / lithium aluminum hydride / tetrahydrofuran / 12 h / Heating
4.1: 77 percent / NaBH4; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C
5.1: NaH / dimethylformamide / 0.08 h / 0 °C
5.2: 83 percent / dimethylformamide / 2 h
6.1: 68 percent / H2 / Pd/C / methanol / 2 h / 2068.59 Torr
7.1: NaH / dimethylformamide / 0.08 h / 20 °C
7.2: 87 percent / dimethylformamide / 0.5 h
8.1: CH2Cl2 / 2 h / 20 °C
9.1: 0.505 g / NH3 / CH2Cl2 / 0.17 h / 20 °C
View Scheme
参考文献
Smart, Brian P.; Oslund, Rob C.; Walsh, Laura A.; Gelb, Michael H.
Journal of Medicinal Chemistry, 2006 , vol. 49, # 10 p. 2858 - 2860
反应条件
1.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 - 20 °C
1.2: 89 percent / hexane; tetrahydrofuran / 12.5 h / -78 - 20 °C
2.1: 62 percent / lithium aluminum hydride / tetrahydrofuran / 12 h / Heating
3.1: 77 percent / NaBH4; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C
4.1: NaH / dimethylformamide / 0.08 h / 0 °C
4.2: 83 percent / dimethylformamide / 2 h
5.1: 68 percent / H2 / Pd/C / methanol / 2 h / 2068.59 Torr
6.1: NaH / dimethylformamide / 0.08 h / 20 °C
6.2: 87 percent / dimethylformamide / 0.5 h
7.1: CH2Cl2 / 2 h / 20 °C
8.1: 0.505 g / NH3 / CH2Cl2 / 0.17 h / 20 °C
View Scheme
参考文献
Smart, Brian P.; Oslund, Rob C.; Walsh, Laura A.; Gelb, Michael H.
Journal of Medicinal Chemistry, 2006 , vol. 49, # 10 p. 2858 - 2860
反应条件
1.1: NaOH / ethanol / 8 h / Heating
2.1: 2.42 g / K2CO3 / acetonitrile / Heating
3.1: 70 percent / TBAF*3H2O / PdCl2(PPh3)2 / 60 °C
4.1: 67 percent / 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride; t-BuOK / Pd(OAc)2 / toluene / Heating
5.1: BBr3 / CH2Cl2 / 16 h / -78 - 20 °C
5.2: 81 percent / KHCO3 / CH2Cl2; methanol / 1 h / 0 - 20 °C
6.1: 78 percent / NaH / dimethylformamide / 20 °C
7.1: CH2Cl2 / 2 h / 20 °C
7.2: 75 percent / 1,1,1,3,3,3-hexamethyldisilazane / CH2Cl2 / 20 °C
View Scheme
参考文献
Sanz, Roberto; Castroviejo, M. Pilar; Guilarte, Veronica; Perez, Antonio; Fananas, Francisco J.
Journal of Organic Chemistry, 2007 , vol. 72, # 14 p. 5113 - 5118
反应条件
1.1: lithium 2,2,6,6-tetramethylpiperidine; t-Bu2Zn / tetrahydrofuran / -78 - -30 °C
1.2: 78 percent / I2 / tetrahydrofuran / 2 h / 20 °C
2.1: 70 percent / TBAF*3H2O / PdCl2(PPh3)2 / 60 °C
3.1: 67 percent / 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride; t-BuOK / Pd(OAc)2 / toluene / Heating
4.1: BBr3 / CH2Cl2 / 16 h / -78 - 20 °C
4.2: 81 percent / KHCO3 / CH2Cl2; methanol / 1 h / 0 - 20 °C
5.1: 78 percent / NaH / dimethylformamide / 20 °C
6.1: CH2Cl2 / 2 h / 20 °C
6.2: 75 percent / 1,1,1,3,3,3-hexamethyldisilazane / CH2Cl2 / 20 °C
View Scheme
参考文献
Sanz, Roberto; Castroviejo, M. Pilar; Guilarte, Veronica; Perez, Antonio; Fananas, Francisco J.
Journal of Organic Chemistry, 2007 , vol. 72, # 14 p. 5113 - 5118
