Methyl 4-Iodophenylacetate → Methyl{4-[3-isopropyl-4-(1-methyl-cyclopropoxymethyl)-phenylethynyl)-phenyl}-acetate

HRID 1861513Notes

Reaction equation

HRID 1861513 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][O:10][C:11]2([CH3:14])[CH2:13][CH2:12]2)=[C:5]([CH:15]([CH3:17])[CH3:16])[CH:4]=1)#[CH:2].[CH3:18][O:19][C:20](=[O:29])[CH2:21][C:22]1[CH:27]=[CH:26][C:25](I)=[CH:24][CH:23]=1>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:15]([C:5]1[CH:4]=[C:3]([C:1]#[C:2][C:25]2[CH:26]=[CH:27][C:22]([CH2:21][C:20]([O:19][CH3:18])=[O:29])=[CH:23][CH:24]=2)[CH:8]=[CH:7][C:6]=1[CH2:9][O:10][C:11]1([CH3:14])[CH2:12][CH2:13]1)([CH3:17])[CH3:16]

Participants

6

Reactant 2

HCID 10378700Methyl 4-Iodophenylacetate2×HCID 18710218HCID 18710218, compound2×

Product 1

HCID 86585939Methyl{4-[3-isopropyl-4-(1-methyl-cyclopropoxymethyl)-phenylethynyl)-phenyl}-acetateYield 60.2%

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-2-isopropyl-1-(1-methyl-cyclopropoxymethyl)-benzene (Intermediate 166, 78.0 mg, 0.34 mmol) and methyl-(4-iodophenyl)-acetate (Reagent B, 94.0 mg, 0.34 mmol) in triethylamine (8 mL) was treated with copper(I)iodide (22.0 mg, 0.11 mmol) and sparged with argon for 5 minutes. Dichlorobis(triphenylphosphine)palladium(II) (79 mg, 0.11 mmol) was added and the reaction mixture was stirred at room temperature for 3.5 hours. Column chromatography (2-5% EtOAc-hexanes) afforded 77.0 mg (60%) of the title compound as a yellow oil.

Workup

  1. customsparged with argon for 5 minutes

Sources & evidence

ORD record
ord-68eb34e5a5424dfd904e6e50ff016947
Source dataset
uspto-grants-2003_03
Patent number
US06531599B2

Reaction notes

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