Methyl 4-Iodophenylacetate → Methyl[4-(4-imidazol-1-yl-methyl-3-methyl-phenylethynyl)-phenyl]-acetate

HRID 1936154Notes

Reaction equation

HRID 1936154 reaction equation
[C:1]([C:3]1C=[CH:13][C:6]([CH2:7][N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)=[C:5]([CH3:15])[CH:4]=1)#[CH:2].[CH3:16][O:17][C:18](=[O:27])[CH2:19][C:20]1[CH:25]=[CH:24]C(I)=[CH:22][CH:21]=1.CO.[CH3:30][CH2:31]OC(C)=O>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>[N:8]1([C:7]2[CH:31]=[CH:30][C:4]([C:3]#[C:1][C:2]3[CH:22]=[CH:21][C:20]([CH2:19][C:18]([O:17][CH3:16])=[O:27])=[CH:25][CH:24]=3)=[C:5]([CH3:15])[C:6]=2[CH3:13])[CH:12]=[CH:11][N:10]=[CH:9]1

Participants

7

Reactant 3

HCID 10378700Methyl 4-Iodophenylacetate2×HCID 21584119Ethylacetate methanolHCID 22568804HCID 22568804, compound2×

Product 1

HCID 86585931Methyl[4-(4-imidazol-1-yl-methyl-3-methyl-phenylethynyl)-phenyl]-acetateYield 25%

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; 1-(4-ethynyl-2-methyl-benzyl)-1H-imidazole (Intermediate 141, 101.0 mg, 0.53 mmol) and methyl-(4-iodophenyl)-acetate (Reagent B, 145.0 mg, 0.53 mmol) in triethylamine (5 mL) was treated with copper(I)iodide (34.0 mg, 0.18 mmol) and sparged with argon for 5 minutes. Dichlorobis(triphenylphosphine)palladium(II) (124 mg, 0.18 mmol) was added and the reaction mixture was stirred overnight at room temperature. Column chromatography (5% MeOH-EtOAc) afforded 45.0 mg (25%) of the title compound as an orange oil.

Workup

  1. customsparged with argon for 5 minutes

Sources & evidence

ORD record
ord-b3bda8bf36c84b91b98816db44cb13cd
Source dataset
uspto-grants-2002_05
Patent number
US06387951B1

Reaction notes

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