Diisopropylamine → HCID 86629305, compound

HRID 1039491Notes

Reaction equation

HRID 1039491 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][C:7](/[C:10](/[C:26]3[CH:31]=[CH:30][C:29]([C:32]#[C:33][CH2:34][N:35]4[CH2:40]COC[CH2:36]4)=[CH:28][CH:27]=3)=[CH:11]/[CH2:12][O:13][C:14]3[CH:24]=[CH:23][C:17]([O:18][CH2:19][C:20]([OH:22])=[O:21])=[C:16]([CH3:25])[CH:15]=3)=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.[CH3:41]N(CC#C)C.C(NC(C)C)(C)C>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>[CH:1]1([C:4]2[CH:9]=[CH:8][C:7](/[C:10](/[C:26]3[CH:31]=[CH:30][C:29]([C:32]#[C:33][CH2:34][N:35]([CH3:36])[CH3:40])=[CH:28][CH:27]=3)=[CH:11]/[CH2:12][O:13][C:14]3[CH:24]=[CH:23][C:17]([O:18][CH2:19][C:20]([O:22][CH3:41])=[O:21])=[C:16]([CH3:25])[CH:15]=3)=[CH:6][CH:5]=2)[CH2:2][CH2:3]1

Participants

7

Reactant 3

HCID 7912DiisopropylamineHCID 81643N,N-DimethylpropargylamineHCID 23633777HCID 23633777, compound

Product 1

HCID 86629305HCID 86629305, compound

Reagents, catalysts & solvents 3

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

Procedure

To a degassed solution of the ester (486 mg, 0.877 mmol; prepared as described in example 38), 1-(N,N-dimethylamino)prop-2-yne (150 mg, 1.80 mmol) and diisopropyl amine (0.589 mL, 4.24 mmol) in anhydrous tetrahydrofuran (12 mL), bis(triphenylphosphine)palladium(II) dichloride (47 mg, 0.067 mmol) and copper(I) iodide (14.0 mg, 0.074 mmol) were added. The reaction mixture was stirred at ambient temperature for 6 h under nitrogen. The solvents were evaporated in vacuo and the residue was purified by flash column chromatography (silica gel Fluka 60, chloroform/methanol 100:0-95:5) yielding methyl (Z)-[4-[3-(4-cyclopropylphenyl)-3-[4-[3-(N,N-dimethylamino)propynyl]phenyl]allyloxy]-2-methylphenoxy]acetate as yellow oil.

Workup

  1. customThe solvents were evaporated in vacuo
  2. customthe residue was purified by flash column chromatography (silica gel Fluka 60, chloroform/methanol 100:0-95:5)

Sources & evidence

ORD record
ord-7ac0c31ab7e04120a53b12358de410fe
Source dataset
uspto-grants-2013_10
Patent number
US08551993B2

Reaction notes

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