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

HRID 17539
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HRID 17539 반응식
[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]
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참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매
HCID 178418476
HCID 178418476, 화합물
촉매
HCID 312751,4-Dioxane용매

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온도
30 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-edb7512fe008400fbb309091a2445737
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07737166B2

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