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

HRID 2185272Notes

Reaction equation

HRID 2185272 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].[CH2:14]([O:16][C:17](=[O:25])[C:18]1[CH:23]=[CH:22][C:21](I)=[CH:20][CH:19]=1)[CH3:15]>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]([C:17]([O:16][CH2:14][CH3:15])=[O:25])=[CH:19][CH:20]=3)=[CH:4][CH:5]=2)[CH2:10][CH2:11]1

Participants

6

Reactant 2

HCID 142891Ethyl 4-iodobenzoate2×HCID 225689501-Ethynyl-4-(1-methoxycyclopropyl)-benzene2×

Product 1

HCID 22568838Ethyl 4-[4-(1-methoxycyclopropyl)-phenylethynyl]-benzoateYield 90%

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, 100.0 mg, 0.47 mmol) and ethyl-4-iodo benzoate (Reagent A, 141.0 mg, 0.51 mmol) in triethyl amine (6 mL) was treated with copper(I)iodide (30.0 mg, 0.16 mmol) and sparged with argon for 5 minutes. Dichlorobis(triphenylphosphine)palladium(II) (109 mg, 0.16 mmol) was added and the reaction mixture was stirred overnight at room temperature. Column chromatography (2-5% EtOAc-hexanes) afforded 135.0 mg (90%) of the title compound as an orange solid.

Workup

  1. customsparged with argon for 5 minutes

Sources & evidence

ORD record
ord-a2fba90796f746969457069ef9714bd5
Source dataset
uspto-grants-2002_06
Patent number
US06399774B1

Reaction notes

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