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

HRID 2185273Notes

Reaction equation

HRID 2185273 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2([O:12][CH3:13])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[CH:2].[CH3:14][O:15][C:16](=[O:25])[CH2:17][C:18]1[CH:23]=[CH:22][C:21](I)=[CH:20][CH:19]=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>[CH3:13][O:12][C:9]1([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[C:2][C:21]3[CH:22]=[CH:23][C:18]([CH2:17][C:16]([O:15][CH3:14])=[O:25])=[CH:19][CH:20]=3)=[CH:4][CH:5]=2)[CH2:10][CH2:11]1

Participants

6

Reactant 2

HCID 10378700Methyl 4-Iodophenylacetate2×HCID 225689501-Ethynyl-4-(1-methoxycyclopropyl)-benzene2×

Product 1

HCID 86585921Methyl{4-[4-(1-methoxycyclopropyl)-phenylethynyl]-phenyl}-acetateYield 78%

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-methoxycyclopropyl)-benzene (Intermediate 61, 120.0 mg, 0.56 mmol) and methyl-(4-iodophenyl)-acetate (Reagent B, 154.0 mg, 0.56 mmol) in triethyl amine (6 mL) was treated with copper(I)iodide (35.0 mg, 0.19 mmol) and sparged with argon for 5 minutes. Dichlorobis(triphenylphosphine)palladium(II) (130 mg, 0.19 mmol) was added and the reaction mixture was stirred overnight at room temperature. Column chromatography (2-8% EtOAc-hexanes) afforded 140.0 mg (78%) of the title compound as an orange solid.

Workup

  1. customsparged with argon for 5 minutes

Sources & evidence

ORD record
ord-7300e03baac5457c91aa4e2cddf352fc
Source dataset
uspto-grants-2002_06
Patent number
US06399774B1

Reaction notes

Loading…