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

HRID 17539

反応式

HRID 17539 の反応式
[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]

参加物

7

反応物 3

HCID 8471TriethylamineHCID 135123,3-Dimethyl-1-butyneHCID 86097515Methyl 4-acetylamino-5-bromo-3-iodosalicylate

生成物 1

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

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
30 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-edb7512fe008400fbb309091a2445737
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

関連ノート

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