Methyl 4-Iodophenylacetate → Methyl{4-[4-(1-benzyloxycyclopropyl)-phenylethynyl]-phenyl}-acetate

HRID 24153Notes

Reaction equation

HRID 24153 reaction equation
[CH:1]([O:4][C:5]1([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]3[CH:26]=[CH:25][C:19](C(OCC)=O)=[CH:18][CH:17]=3)=[CH:10][CH:9]=2)[CH2:7][CH2:6]1)([CH3:3])C.[CH3:27][O:28][C:29](=[O:38])[CH2:30]C1C=CC(I)=CC=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>[CH3:27][O:28][C:29](=[O:38])[CH2:30][C:19]1[CH:25]=[CH:26][C:16]([C:15]#[C:14][C:11]2[CH:10]=[CH:9][C:8]([C:5]3([O:4][CH2:1][C:3]4[CH:9]=[CH:8][CH:5]=[CH:6][CH:7]=4)[CH2:7][CH2:6]3)=[CH:13][CH:12]=2)=[CH:17][CH:18]=1

Participants

6

Reactant 2

HCID 10378700Methyl 4-Iodophenylacetate2×HCID 22568976Ethyl4-[4-(1-isopropoxycyclopropyl)-phenylethynyl]-benzoate2×

Product 1

HCID 86585923Methyl{4-[4-(1-benzyloxycyclopropyl)-phenylethynyl]-phenyl}-acetateYield 161.4%

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-ethynyl-4-(1-benzyloxycyclopropyl)-benzene (Intermediate 71, 60.0 mg, 0.20 mmol) and methyl-(4-iodophenyl)-acetate (Reagent B, 66.0 mg, 0.24 mmol) in triethylamine (5 mL) was treated with copper(I)iodide (15.0 mg, 0.08 mmol) and sparged with argon for 5 minutes. Dichlorobis(triphenylphosphine)palladium(II) (56 mg, 0.08 mmol) was added and the reaction mixture was stirred overnight at room temperature. Column chromatography (2-7% EtOAc—hexanes) afforded 64.0 mg (81%) of the title compound as a yellow oil.

Workup

  1. customsparged with argon for 5 minutes

Sources & evidence

ORD record
ord-bac3e1e841bf4a9fa40f79227e822422
Source dataset
uspto-grants-2005_02
Patent number
US06855512B2

Reaction notes

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