反应方程式
Br[C:2]1[S:6][C:5]([S:7]([NH2:10])(=[O:9])=[O:8])=[CH:4][CH:3]=1.C(N(CC)CC)C.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C]=O.[C:49]([O:52][CH2:53]C)(=[O:51])C>CN(C)C=O.[Cl-].[Na+].O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CO>[CH3:53][O:52][C:49]([C:2]1[S:6][C:5]([S:7]([NH2:10])(=[O:9])=[O:8])=[CH:4][CH:3]=1)=[O:51]参与物
反应物 5
产物 1
试剂、催化剂与溶剂 4
反应条件
- 温度
- 100 °C
实验过程
A mixture of 5-bromothiophene-2-sulfonamide (0.50 g, 2.1 mmol), triethyl amine (1 mL), methanol (1 mL), palladium acetate (0.046 g, 2.1 mmol) and 1,3-bis(diphenylphosphino) propane (0.085 g, 2.1 mmol) (addition in that order) in dimethylformamide (5 mL, anhydrous) is saturated with carbon monoxide gas, at room temperature. This reaction mixture is heated to 100° C. and stirred overnight, under a carbon monoxide atmosphere. 10 mL of brine and 10 mL of ethyl acetate are added to the reaction mixture. The organic phase is separated and the aqueous layer is extracted with 10 mL ethyl acetate. The combined organic layers are dried over sodium sulfate, concentrated in vacuo, and then chromatographed on silica (0–1% methyl alcohol in methylene chloride) to give the title compound, as a yellow solid (0.15 g, 34% yield).
后处理
- customThe organic phase is separated
- extractionthe aqueous layer is extracted with 10 mL ethyl acetate
- dry with materialThe combined organic layers are dried over sodium sulfate
- concentrationconcentrated in vacuo
- customchromatographed on silica (0–1% methyl alcohol in methylene chloride)
来源与证据
- ORD记录
- ord-7b3ef08a6ec846058fe20b3dbccc2c1d
- 来源数据集
- uspto-grants-2006_08
- 专利号
- US07084170B2
关联笔记
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