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Tetrahydrofuran → methyl (Z)-[2-methyl-4-[3-(4-methylphenyl)-3-[4-(3-pyrazol-1-ylpropynyl)phenyl]allyloxy]phenoxy]acetate

HRID 1039459
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HRID 1039459 반응식
[CH3:1][C:2]1[CH:12]=[C:11]([O:13][CH2:14]/[CH:15]=[C:16](/[C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)\[C:17]2[CH:22]=[CH:21][C:20]([C:23]#[C:24][CH2:25][N:26]3CCO[CH2:28][CH2:27]3)=[CH:19][CH:18]=2)[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=O.C([N:42]1[CH:46]=CC=N1)C#C.[O:47]1CCC[CH2:48]1>C(N(CC)CC)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[CH3:1][C:2]1[CH:12]=[C:11]([O:13][CH2:14]/[CH:15]=[C:16](/[C:32]2[CH:33]=[CH:34][C:35]([CH3:38])=[CH:36][CH:37]=2)\[C:17]2[CH:22]=[CH:21][C:20]([C:23]#[C:24][CH2:25][N:26]3[CH:27]=[CH:28][CH:46]=[N:42]3)=[CH:19][CH:18]=2)[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([O:47][CH3:48])=[O:8]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 8028TetrahydrofuranHCID 117685231-(prop-2-yn-1-yl)-1H-pyrazoleHCID 23633919(Z)-[2-Methyl-4-[3-(4-methylphenyl)-3-[4-[3-(morpholin-4-yl)propynyl]phenyl]allyloxy]-phenoxy]acetic Acid

생성물 1

HCID 86629289methyl (Z)-[2-methyl-4-[3-(4-methylphenyl)-3-[4-(3-pyrazol-1-ylpropynyl)phenyl]allyloxy]phenoxy]acetate

시약·촉매·용매 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
촉매
HCID 178418397HCID 178418397, 화합물촉매
HCID 8471Triethylamine용매

실험 절차

A solution of methyl (Z)-[2-methyl-4-[3(4-iodophenyl)-3-(4-methylphenyl)]allyloxy]-phenoxy]acetate (310 mg, 0.587 mmol; example 3) in a mixture of tetrahydrofuran (9 mL) and triethylamine (9 mL) was degassed and 1-propargyl-1H-pyrazole (124 mg, 1.17 mmol) was added in argon atmosphere. The solution was cooled down; tetrakis(triphenylphosphine)palladium (54 mg, 0.046 mmol) and copper(I) iodide (17.8 mg, 0.094 mmol) were added. The reaction mixture was stirred at ambient temperature for 4 days, subsequently evaporated in vacuo and the residue was dissolved in ethyl acetate (20 mL). The solution was washed with water (3×15 mL), dried with anhydrous magnesium sulphate and evaporated in vacuo. The residue was purified by flash column chromatography (silica gel Fluka 60, hexanes/ethyl acetate 7:3) yielding methyl (Z)-[2-methyl-4-[3(4-methylphenyl)-3-[4-(3-pyrazol-1-ylpropynyl)phenyl]allyloxy]phenoxy]acetate.

후처리

  1. customwas degassed
  2. temperatureThe solution was cooled down
  3. customsubsequently evaporated in vacuo
  4. dissolutionthe residue was dissolved in ethyl acetate (20 mL)
  5. washThe solution was washed with water (3×15 mL)
  6. dry with materialdried with anhydrous magnesium sulphate
  7. customevaporated in vacuo
  8. customThe residue was purified by flash column chromatography (silica gel Fluka 60, hexanes/ethyl acetate 7:3)

출처 및 근거

ORD 기록
ord-777ab7f268e74117b1a11ced52f6e57c
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08551993B2

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