Triethylamine → Ethyl4-[4-(1-isopropoxycyclopropyl)-3-methyl-phenylethynyl]-benzoate

HRID 395121Notes

Reaction equation

HRID 395121 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2([O:12][CH:13]([CH3:15])[CH3:14])[CH2:11][CH2:10]2)=[CH:5][C:4]=1C)#[CH:2].[CH2:17]([O:19][C:20](=[O:28])[C:21]1[CH:26]=[CH:25][C:24](I)=[CH:23][CH:22]=1)[CH3:18].[CH2:29](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:13]([O:12][C:9]1([C:6]2[CH:5]=[CH:4][C:3]([C:1]#[C:2][C:24]3[CH:25]=[CH:26][C:21]([C:20]([O:19][CH2:17][CH3:18])=[O:28])=[CH:22][CH:23]=3)=[CH:8][C:7]=2[CH3:29])[CH2:10][CH2:11]1)([CH3:14])[CH3:15]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 142891Ethyl 4-iodobenzoate2×HCID 225689974-Ethynyl-1-(1-isopropoxycyclopropyl)-3-methyl-benzene2×

Product 1

HCID 22568844Ethyl4-[4-(1-isopropoxycyclopropyl)-3-methyl-phenylethynyl]-benzoateYield 56%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

Using General Procedure F; 4-ethynyl-1-(1-isopropoxycyclopropyl)-3-methyl-benzene (Intermediate 81, 80.0 mg, 0.13 mmol) and ethyl-4-iodo benzoate (Reagent A, 100.0 mg, 0.36 mmol) in triethylamine (5 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 (2-4% EtOAc-hexanes) afforded 75.0 mg (56%) of the title compound as an orange solid.

Workup

  1. customsparged with argon for 5 minutes

Sources & evidence

ORD record
ord-0a20fca871e943659e8cb5027b98a79f
Source dataset
uspto-grants-2003_08
Patent number
US06603019B2

Reaction notes

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