Methyl 4-Iodophenylacetate → Methyl{4-[4-(1-ethoxycyclopropyl)-3-tert-butyl-phenylethynyl]-phenyl}-acetate

HRID 841450Notes

Reaction equation

HRID 841450 reaction equation
[CH2:1]([O:3][C:4]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]#[CH:14])=[CH:9][C:8]=2[C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:6][CH2:5]1)[CH3:2].[CH3:19][O:20][C:21](=[O:30])[CH2:22][C:23]1[CH:28]=[CH:27][C:26](I)=[CH:25][CH:24]=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>[CH3:19][O:20][C:21](=[O:30])[CH2:22][C:23]1[CH:24]=[CH:25][C:26]([C:14]#[C:13][C:10]2[CH:11]=[CH:12][C:7]([C:4]3([O:3][CH2:1][CH3:2])[CH2:6][CH2:5]3)=[C:8]([C:15]([CH3:17])([CH3:16])[CH3:18])[CH:9]=2)=[CH:27][CH:28]=1

Participants

6

Reactant 2

HCID 10378700Methyl 4-Iodophenylacetate2×HCID 225688751-(1-Ethoxycyclopropyl)-4-ethynyl-2-tert-butylbenzene2×

Product 1

HCID 86585930Methyl{4-[4-(1-ethoxycyclopropyl)-3-tert-butyl-phenylethynyl]-phenyl}-acetateYield 72%

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-(1-ethoxycyclopropyl)-4-ethynyl-2-tert-butylbenzene (Intermediate 112, 95.0 mg, 0.39 mmol) and methyl-(4-iodophenyl)-acetate (Reagent B, 108.0 mg, 0.39 mmol) in triethylamine (8 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 (2-5% EtOAc-hexanes) afforded 100.0 mg (72%) of the title compound.

Workup

  1. customsparged with argon for 5 minutes

Sources & evidence

ORD record
ord-04d47525b0b9474c976cccd2d7274d44
Source dataset
uspto-grants-2002_04
Patent number
US06369225B1

Reaction notes

Loading…