Ethyl 4-iodobenzoate → Ethyl4-[4-(1-benzyloxycyclopropyl)-phenylethynyl]-benzoate

HRID 24152Notes

Reaction equation

HRID 24152 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:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=3)=[CH:10][CH:9]=2)[CH2:7][CH2:6]1)([CH3:3])C.C(OC(=O)[C:31]1[CH:36]=[CH:35]C(I)=[CH:33][CH:32]=1)C>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>[CH2:1]([O:4][C:5]1([C:8]2[CH:9]=[CH:10][C:11]([C:14]#[C:15][C:16]3[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=3)=[CH:12][CH:13]=2)[CH2:7][CH2:6]1)[C:3]1[CH:35]=[CH:36][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 2

HCID 142891Ethyl 4-iodobenzoate2×HCID 22568976Ethyl4-[4-(1-isopropoxycyclopropyl)-phenylethynyl]-benzoate2×

Product 1

HCID 22568905Ethyl4-[4-(1-benzyloxycyclopropyl)-phenylethynyl]-benzoateYield 91%

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, 0.24 mmol) and ethyl-4-iodo benzoate (Reagent A, 72.0 mg, 0.26 mmol) in triethylamine (4 mL) was treated with copper(I)iodide (17.0 mg, 0.09 mmol) and sparged with argon for 5 minutes. Dichlorobis(triphenylphosphine)palladium(II) (61 mg, 0.09 mmol) was added and the reaction mixture was stirred overnight at room temperature. Column chromatography (2-4% EtOAc—hexanes) afforded 85.0 mg (91%) of the title compound as an orange oil.

Workup

  1. customsparged with argon for 5 minutes

Sources & evidence

ORD record
ord-867652077ff241399f602148dffaa87f
Source dataset
uspto-grants-2005_02
Patent number
US06855512B2

Reaction notes

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