反应方程式
CC(C)(C)OC(=O)N1CCNCC1.CS(=O)(=O)c1ccc(COc2ccc(Br)cn2)cc1>CC(C)(C)[O-].Cc1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Na+].[Pd].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>CC(C)(C)OC(=O)N1CCN(c2ccc(OCc3ccc(S(C)(=O)=O)cc3)nc2)CC1参与物
反应物 2
产物 1
试剂、催化剂与溶剂 4
反应条件
- 温度
- 80 °C
实验过程
2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (48.3 mg, 0.08 mmol) was added in one portion to 5-bromo-2-(4-(methylsulfonyl)benzyloxy)pyridine (257.9 mg, 0.75 mmol), tert-butyl piperazine-1-carboxylate (160.9 mg, 0.86 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (51.1 mg, 0.06 mmol) and sodium 2-methylpropan-2-olate (120.1 mg, 1.25 mmol) in toluene (10 mL). N2 was bubbled through the solvent for 15 minutes.The resulting mixture was stirred at 80 °C for over night under N2.The reaction mixture was filtered through celite. The reaction mixture was evaporated to dryness and redissolved in EtOAc (75 mL), and washed sequentially with water (2x75 mL) and saturated brine (100 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 70% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford tert-butyl 4-(6-(4-(methylsulfonyl)benzyloxy)pyridin-3-yl)piperazine-1-carboxylate (42.6 %) as a yellow solid.
来源与证据
- ORD记录
- ord-b165e514f9f846c2872fe8f816e6b2d7
- 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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