Diisopropylamine → HCID 86629315, compound

HRID 549887Notes

Reaction equation

HRID 549887 reaction equation
[CH2:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][OH:11])[CH2:6][CH2:5]1)[C:2]#[CH:3].C(NC(C)C)(C)C.[Cl:19][C:20]1[CH:25]=[CH:24][C:23](/[C:26](/[C:43]2[CH:48]=[CH:47][C:46](I)=[CH:45][CH:44]=2)=[CH:27]/[CH2:28][O:29][C:30]2[CH:41]=[CH:40][C:33]([O:34][CH2:35][C:36]([O:38][CH3:39])=[O:37])=[C:32]([CH3:42])[CH:31]=2)=[CH:22][CH:21]=1>O1CCCC1.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>[Cl:19][C:20]1[CH:21]=[CH:22][C:23](/[C:26](/[C:43]2[CH:44]=[CH:45][C:46]([C:3]#[C:2][CH2:1][N:4]3[CH2:9][CH2:8][CH:7]([CH2:10][OH:11])[CH2:6][CH2:5]3)=[CH:47][CH:48]=2)=[CH:27]/[CH2:28][O:29][C:30]2[CH:41]=[CH:40][C:33]([O:34][CH2:35][C:36]([O:38][CH3:39])=[O:37])=[C:32]([CH3:42])[CH:31]=2)=[CH:24][CH:25]=1

Participants

7

Reactant 3

HCID 7912DiisopropylamineHCID 18616662(1-(Prop-2-yn-1-yl)piperidin-4-yl)methanolHCID 86629280HCID 86629280, compound

Product 1

HCID 86629315HCID 86629315, compound

Reagents, catalysts & solvents 3

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

Procedure

Under nitrogen atmosphere, (1-propargylpiperidin-4-yl)methanol (122 mg, 0.8 mmol) and diisopropylamine (370 mg, 0.56 mmol) were added to a degassed solution of methyl (Z)-[4-[3-(4-chlorophenyl)-3-(4-iodophenyl)allyloxy]-2-methylphenoxy]acetate (220 mg, 0.4 mmol; prepared as described in example 7) in tetrahydrofuran (15 mL). Subsequently, bis(triphenylphosphine)palladium(II) dichloride (30 mg, 0.042 mmol) and copper(I) iodide (15 mg, 0.075 mmol) were added; the reaction mixture was degassed again and then stirred under inert atmosphere at ambient temperature over night. The reaction mixture was diluted with ethyl acetate (20 mL) and filtered through a paddle of silica gel. The paddle was thoroughly washed with ethyl acetate (4×20 mL) and the combined filtrates were concentrated in vacuo. The residue was purified by column chromatography (silica gel Fluka 60, chloroform/methanol 95:5) yielding methyl (E)-[4-[3-(4-chlorophenyl)-3-[4-[3-[4-(hydroxymethyl)piperidin-1-yl]propynyl]phenyl]allyloxy]-2-methyl phenoxy]acetate.

Workup

  1. customthe reaction mixture was degassed again
  2. additionThe reaction mixture was diluted with ethyl acetate (20 mL)
  3. filtrationfiltered through a paddle of silica gel
  4. washThe paddle was thoroughly washed with ethyl acetate (4×20 mL)
  5. concentrationthe combined filtrates were concentrated in vacuo
  6. customThe residue was purified by column chromatography (silica gel Fluka 60, chloroform/methanol 95:5)

Sources & evidence

ORD record
ord-1a56294a8b864caab87fbb4c53b1a3a9
Source dataset
uspto-grants-2011_05
Patent number
US07943613B2

Reaction notes

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