7-溴苯并呋喃-2-羧酸乙酯 → Ethyl 7-(4-(2-(1-acetylindolin-5-yl)ethyl)piperazin-1-yl)benzofuran-2-carboxylate

HRID 97笔记

反应方程式

HRID 97 反应方程式
CC(=O)N1CCc2cc(CCN3CCNCC3)ccc21.CCOC(=O)c1cc2cccc(Br)c2o1>C1COCCO1.CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd].[Pd]>CCOC(=O)c1cc2cccc(N3CCN(CCc4ccc5c(c4)CCN5C(C)=O)CC3)c2o1

参与物

7

反应物 2

HCID 467388337-溴苯并呋喃-2-羧酸乙酯HCID 596367471-(5-(2-(Piperazin-1-yl)ethyl)indolin-1-yl)ethanone

产物 1

HCID 59636756Ethyl 7-(4-(2-(1-acetylindolin-5-yl)ethyl)piperazin-1-yl)benzofuran-2-carboxylate收率 64.44%

试剂、催化剂与溶剂 4

HCID 10796碳酸氢铯试剂HCID 9811564三(二亚苄基丙酮)二钯催化剂HCID 111557942-二环己基膦-2',4',6'-三异丙基联苯催化剂HCID 312751,4-二氧六环溶剂

反应条件

温度
95 °C

实验过程

22/04 2009 09:43:42 +0200 To ethyl 7-bromobenzofuran-2-carboxylate (0.095 g, 0.35 mmol) and 1-(5-(2-(piperazin-1-yl)ethyl)indolin-1-yl)ethanone (0.101 g, 0.37 mmol) (from EN02198-74) in dry degassed dioxane (1.5 mL) were added Cesium carbonate (0.150 g, 0.46 mmol), 2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.017 g, 0.04 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (0.016 g, 0.02 mmol) under argon and the reaction heated at 95°C for 5.5h. After cooling to rt, water and DCM were added and the layers separated. The aq phase was extracted with DCM (3x). The combined org phases were washed with water, dried (MgSO4), filtered and evaporated. The crude was purified by flash (SiO2; DCM/MeOH 95/5) to give 0.105 g of the product as a yellow solid.

来源与证据

ORD记录
ord-09c188bd82d940b1aa9d4223b96f551d
来源数据集
750 AstraZeneca ELN dataset
原始链接
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反应笔记

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