Diisopropylamine → methyl (E)-[2-methyl-4-[3-[4-[3-(N,N-dimethylamino)propynyl]phenyl]-3-(4-trifluoromethylphenyl)allyloxy]phenoxy]acetate

HRID 1039462Notes

Reaction equation

HRID 1039462 reaction equation
[CH3:1][N:2]([CH2:4][C:5]#[CH:6])[CH3:3].C(NC(C)C)(C)C.I[C:15]1[CH:20]=[CH:19][C:18](/[C:21](/[C:38]2[CH:43]=[CH:42][C:41]([C:44]([F:47])([F:46])[F:45])=[CH:40][CH:39]=2)=[CH:22]\[CH2:23][O:24][C:25]2[CH:36]=[CH:35][C:28]([O:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[C:27]([CH3:37])[CH:26]=2)=[CH:17][CH:16]=1>O1CCCC1.[Cu]I.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>[CH3:37][C:27]1[CH:26]=[C:25]([O:24][CH2:23]/[CH:22]=[C:21](\[C:18]2[CH:17]=[CH:16][C:15]([C:6]#[C:5][CH2:4][N:2]([CH3:3])[CH3:1])=[CH:20][CH:19]=2)/[C:38]2[CH:43]=[CH:42][C:41]([C:44]([F:47])([F:46])[F:45])=[CH:40][CH:39]=2)[CH:36]=[CH:35][C:28]=1[O:29][CH2:30][C:31]([O:33][CH3:34])=[O:32]

Participants

7

Reactant 3

HCID 7912DiisopropylamineHCID 81643N,N-DimethylpropargylamineHCID 86629276methyl (Z)-[4-[3-(4-iodophenyl)-3-(4-trifluoromethylphenyl)allyloxy]-2-methylphenoxy]acetate

Product 1

HCID 86629291methyl (E)-[2-methyl-4-[3-[4-[3-(N,N-dimethylamino)propynyl]phenyl]-3-(4-trifluoromethylphenyl)allyloxy]phenoxy]acetate

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

N,N-Dimethylpropargylamine (0.11 mL, 1.03 mmol) and diisopropylamine (0.34 mL, 2.42 mmol) were added to a solution of methyl (Z)-[4-[3-(4-iodophenyl)-3-(4-trifluoromethylphenyl)allyloxy]-2-methylphenoxy]acetate (300 mg, 0.515 mmol; example 4) in tetrahydrofuran (10 mL). The mixture was degassed and copper(I) iodide (8 mg, 0.042 mmol) and bis(triphenylphosphine)palladium(II) dichloride (18 mg, 0.026 mmol) were added. The reaction mixture was stirred at ambient temperature for 20 h and evaporated in vacuo. The residue was purified by flash column chromatography (silica gel Fluka 60, dichloromethane-/methanol 98:2) yielding methyl (E)-[2-methyl-4-[3-[4-[3-(N,N-dimethylamino)propynyl]-phenyl]-3-(4-trifluoromethylphenyl)allyloxy]phenoxy]acetate as brown oil.

Workup

  1. customThe mixture was degassed
  2. customevaporated in vacuo
  3. customThe residue was purified by flash column chromatography (silica gel Fluka 60, dichloromethane-/methanol 98:2)

Sources & evidence

ORD record
ord-51e8bea11fe74670a08483fa33e898ff
Source dataset
uspto-grants-2013_10
Patent number
US08551993B2

Reaction notes

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