反应方程式
CCOC(=O)c1cnc2cc(OC)c(Br)cc2c1Nc1ccc(Cl)cc1Cl.CN1CCNCC1>C1COCCO1.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].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>CCOC(=O)c1cnc2cc(OC)c(N3CCN(C)CC3)cc2c1Nc1ccc(Cl)cc1Cl参与物
反应物 2
产物 1
试剂、催化剂与溶剂 4
反应条件
- 温度
- 100 °C
实验过程
To a solution of ethyl 6-bromo-4-(2,4-dichlorophenylamino)-7-methoxyquinoline-3-carboxylate (694 mg, 1.48 mmol) and 1-methylpiperazine (0.246 mL, 2.21 mmol) in dioxane (10 mL) was added cesium carbonate (962 mg, 2.95 mmol), tris(dibenzylideneacetone)dipalladium(0) (67.6 mg, 0.07 mmol) and rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (92 mg, 0.15 mmol). Reaction vessel in oil bath set to 100 °C. 2.15pm o/n 20 hours - LCMS shows product (489) and SM (470) 26 hours - ratio of product : SM looks better by MS. 2 x o/n - small SM peak remaining in MS. Concentrated onto silica and purified on ISCO. 40g column, 4:1 H:EA, then gradient up to ~1:1 EA:MeOH. Can't find product by LCMS in any fractions. NMR of polar fractions may be acid from Buchwald coupling. Need to purify SM on column, repeat.
来源与证据
- ORD记录
- ord-805e4c9d19604f5ca8a6f376906a62c5
- 来源数据集
- 750 AstraZeneca ELN dataset
- 原始链接
- 查看来源
关联笔记
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