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

HRID 1039505Notes

Reaction equation

HRID 1039505 reaction equation
[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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

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

Procedure

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-butylphenyl)-3-[4-[3-(pyrazol-1-yl)propynyl]phenyl]allyloxy]-2-methyl-phenoxy]acetate as brown oil.

Workup

  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)

Sources & evidence

ORD record
ord-27201ec73ece4fc39f2fa518eb07e64c
Source dataset
uspto-grants-2013_10
Patent number
US08551993B2

Reaction notes

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