4-Ethynyl-1-(1-isopropoxycyclopropyl)-3-methyl-benzene → HCID 22568844, compound

HRID 51731

Reaction equation

HRID 51731 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2([O:12][CH:13]([CH3:15])[CH3:14])[CH2:11][CH2:10]2)=[CH:5][C:4]=1C)#[CH:2].[C:17](O)(=O)C1C=CC=CC=1.[CH2:26]([O:28][C:29](=[O:37])[C:30]1[CH:35]=[CH:34][C:33](I)=[CH:32][CH:31]=1)[CH3:27]>C(N(CC)CC)C.[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>[CH:13]([O:12][C:9]1([C:6]2[CH:5]=[CH:4][C:3]([C:1]#[C:2][C:33]3[CH:34]=[CH:35][C:30]([C:29]([O:28][CH2:26][CH3:27])=[O:37])=[CH:31][CH:32]=3)=[CH:8][C:7]=2[CH3:17])[CH2:10][CH2:11]1)([CH3:14])[CH3:15]

Participants

6

Reactant 2

HCID 225689974-Ethynyl-1-(1-isopropoxycyclopropyl)-3-methyl-benzene2×HCID 69887287Ethyl-4-iodo-benzoate benzoate2×

Product 1

HCID 22568844HCID 22568844, compoundYield 159.2%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

Using General Procedure F; 4-ethynyl-1-(1-isopropoxycyclopropyl)-3-methyl-benzene (Intermediate 81, 80.0 mg, 0.13 mmol) and ethyl-4-iodo benzoate (Reagent A, 100.0 mg, 0.36 mmol) in triethylamine (5 mL) was treated with copper(I)iodide (25.0 mg, 0.13 mmol) and sparged with argon for 5 minutes. Dichlorobis(triphenylphosphine)-palladium(II) (91 mg, 0.13 mmol) was added and the reaction mixture was stirred overnight at room temperature. Column chromatography (2-4% EtOAc-hexanes) afforded 75.0 mg (56%) of the title compound as an orange solid.

Workup

  1. customsparged with argon for 5 minutes

Sources & evidence

ORD record
ord-8fadf66058e54861ba260ff04d8d7272
Source dataset
uspto-grants-2004_03
Patent number
US06713647B2

Linked notes

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