三乙胺 → Methyl 4-acetylamino-5-bromo-3-(3,3-dimethyl-1-butynyl)salicylate

HRID 17539笔记

反应方程式

HRID 17539 反应方程式
[C:1]([NH:4][C:5]1[C:6](I)=[C:7]([OH:16])[C:8](=[CH:13][C:14]=1[Br:15])[C:9]([O:11][CH3:12])=[O:10])(=[O:3])[CH3:2].[CH3:18][C:19]([CH3:23])([CH3:22])[C:20]#[CH:21].C(N(CC)CC)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.O1CCOCC1>[C:1]([NH:4][C:5]1[C:6]([C:21]#[C:20][C:19]([CH3:23])([CH3:22])[CH3:18])=[C:7]([OH:16])[C:8](=[CH:13][C:14]=1[Br:15])[C:9]([O:11][CH3:12])=[O:10])(=[O:3])[CH3:2]

参与物

7

反应物 3

HCID 8471三乙胺HCID 135123,3-二甲基-1-丁炔HCID 86097515Methyl 4-acetylamino-5-bromo-3-iodosalicylate

产物 1

HCID 86630872Methyl 4-acetylamino-5-bromo-3-(3,3-dimethyl-1-butynyl)salicylate

试剂、催化剂与溶剂 3

HCID 24350碘化亚铜催化剂HCID 178418476HCID 178418476，化合物催化剂HCID 312751,4-二氧六环溶剂

反应条件

温度
30 °C

实验过程

Under nitrogen atmosphere, methyl 4-acetylamino-5-bromo-3-iodosalicylate (I-250) (414 mg, 1.0 mmol), bis(triphenylphosphine)palladium(II) chloride (49 mg, 0.07 mmol), copper(I) iodide (19 mg, 0.1 mmol) and 3,3-dimethyl-1-butyne (0.13 ml, 1.1 mmol) were added to a mixed liquid of triethylamine (4 ml) and dioxane (6 ml), followed by stirring at 30° C. for 2 hours. The reaction liquid was concentrated under reduced pressure, then saturated ammonium chloride water was added to the residue, followed by extraction twice with chloroform, the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate. After filtration and concentration under reduced pressure, the resulting residue was subjected to column, chromatography, and the eluate with n-hexane/ethyl acetate (2:1) gave the entitled compound (243 mg, 66.5) as a white solid.

后处理

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. additionsaturated ammonium chloride water was added to the residue
  4. extractionfollowed by extraction twice with chloroform
  5. washthe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationAfter filtration and concentration under reduced pressure
  8. customthe eluate with n-hexane/ethyl acetate (2:1) gave the entitled compound (243 mg, 66.5) as a white solid

来源与证据

ORD记录
ord-edb7512fe008400fbb309091a2445737
来源数据集
uspto-grants-2010_06
专利号
US07737166B2

反应笔记

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