参与物
| 角色 | 名称 | HCID | 投料 |
|---|
| 反应物 | N-甲基哌嗪 | HCID 53167 | — |
| 反应物 | Ethyl 6-bromo-4-[(2,4-dichlorophenyl)amino]-7-methoxyquinoline-3-carboxylate | HCID 68435446 | — |
| 试剂 | 碳酸氢铯 | HCID 10796 | — |
| 催化剂 | 1,1'-联萘-2,2'-双二苯膦 (BINAP) | HCID 634876 | — |
| 催化剂 | 三(二亚苄基丙酮)二钯 | HCID 9811564 | — |
| 溶剂 | 1,4-二氧六环 | HCID 31275 | — |
| 产物 | Ethyl 4-[(2,4-dichlorophenyl)amino]-7-methoxy-6-(4-methylpiperazin-1-yl)quinoline-3-carboxylate | HCID 68437066 | 0% |
反应步骤
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
| 来源数据集 | 750 AstraZeneca ELN dataset |
|---|
| ORD ID | ord-805e4c9d19604f5ca8a6f376906a62c5 |
|---|
| 来源说明 | 750 AstraZeneca ELN dataset |
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