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Diisopropylamine → methyl (Z)-[4-[3-(4-tert-butyl-phenyl)-3-[4-[3-(pyrazol-1-yl)propynyl]phenyl]allyloxy]-2-methylphenoxy]acetate

HRID 1810681
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HRID 1810681 반응식
[CH2:1]([N:4]1C=CC=N1)[C:2]#C.C(NC(C)C)(C)C.[C:16]([C:20]1[CH:25]=[CH:24][C:23](/[C:26](/[C:42]2[CH:47]=[CH:46][C:45]([C:48]#[C:49][CH2:50][N:51]3[CH2:56]COCC3)=[CH:44][CH:43]=2)=[CH:27]/[CH2:28][O:29][C:30]2[CH:40]=[CH:39][C:33]([O:34][CH2:35][C:36]([OH:38])=O)=[C:32]([CH3:41])[CH:31]=2)=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17].[O:57]1CCC[CH2:58]1>[Cu]I>[C:16]([C:20]1[CH:21]=[CH:22][C:23](/[C:26](/[C:42]2[CH:47]=[CH:46][C:45]([C:48]#[C:49][CH2:50][N:51]3[CH:56]=[CH:2][CH:1]=[N:4]3)=[CH:44][CH:43]=2)=[CH:27]/[CH2:28][O:29][C:30]2[CH:40]=[CH:39][C:33]([O:34][CH2:35][C:36]([O:57][CH3:58])=[O:38])=[C:32]([CH3:41])[CH:31]=2)=[CH:24][CH:25]=1)([CH3:19])([CH3:18])[CH3:17]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 7912DiisopropylamineHCID 8028TetrahydrofuranHCID 117685231-(prop-2-yn-1-yl)-1H-pyrazoleHCID 23633559(Z)-[4-[3-(4-tert-Butylphenyl)-3-[4-[3-(morpholin-4-yl)propynyl]phenyl]allyloxy]-2-methylphenoxy]acetic Acid

생성물 1

HCID 86629317methyl (Z)-[4-[3-(4-tert-butyl-phenyl)-3-[4-[3-(pyrazol-1-yl)propynyl]phenyl]allyloxy]-2-methylphenoxy]acetate

시약·촉매·용매

1
HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매

실험 절차

N-Propargylpyrazole (130 mg, 1.23 mmol) and diisopropylamine (0.40 mL, 2.85 mmol) were added to a solution of methyl (Z)-[4-[3-(4-tert-butylphenyl)-3-(4-iodophenyl)-allyloxy]-2-methylphenoxy]cetate (350 mg, 0.614 mmol; prepared as described in example 30) in tetrahydrofuran (10 mL). The mixture was degassed and copper(I) iodide (10 mg, 0.053 mmol) and bis(triphenylphosphine)alladium(II) dichloride (22 mg, 0.031 mmol) were added. The reaction mixture was stirred at ambient temperature over night, filtered and the filtrate was evaporated in vacuo. The residue was purified by flash column chromatography (silica gel Fluka 60, hexanes/ethyl acetate 4:1-3:1) yielding methyl (Z)-[4-[3-(4-tert-butyl-phenyl)-3-[4-[3-(pyrazol-1-yl)propynyl]phenyl]allyloxy]-2-methyl-phenoxy]acetate as brown oil.

후처리

  1. customThe mixture was degassed
  2. filtrationfiltered
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue was purified by flash column chromatography (silica gel Fluka 60, hexanes/ethyl acetate 4:1-3:1)

출처 및 근거

ORD 기록
ord-8e2e5e5a44394321b19914e3384d3b6e
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08362016B2

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