Ethyl 4-iodobenzoate → HCID 22568957, compound

HRID 381124Notes

Reaction equation

HRID 381124 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2([N:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[CH:2].[CH2:19]([O:21][C:22](=[O:30])[C:23]1[CH:28]=[CH:27][C:26](I)=[CH:25][CH:24]=1)[CH3:20]>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>[CH2:19]([O:21][C:22](=[O:30])[C:23]1[CH:28]=[CH:27][C:26]([C:2]#[C:1][C:3]2[CH:8]=[CH:7][C:6]([C:9]3([N:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])[CH2:10][CH2:11]3)=[CH:5][CH:4]=2)=[CH:25][CH:24]=1)[CH3:20]

Participants

6

Reactant 2

HCID 142891Ethyl 4-iodobenzoate2×HCID 225689121-(4-Ethynylphenyl)-cyclopropyl-dipropylamine2×

Product 1

HCID 22568957HCID 22568957, compound

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-(4-ethynylphenyl)-cyclopropyl]-dipropylamine (Intermediate 123, 34.0 mg, 0.16 mmol) and ethyl-4-iodo benzoate (Reagent A, 59.0 mg, 0.21 mmol) in triethyl amine (6 mL) was treated with copper(I)iodide (13.0 mg, 0.07 mmol) and sparged with argon for 5 minutes. Dichlorobis(triphenylphosphine)palladium(II) (49 mg, 0.07 mmol) was added and the reaction mixture was stirred overnight at room temperature. Column chromatography (2-4% EtOAc-hexanes) afforded the title compound as a yellow oil.

Workup

  1. customsparged with argon for 5 minutes

Sources & evidence

ORD record
ord-d0e3835f552c4b72a4dff9e0b27a8374
Source dataset
uspto-grants-2001_10
Patent number
US06303785B1

Reaction notes

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