HCID 22568868, compound → HCID 22568835, compound

HRID 51787Notes

Reaction equation

HRID 51787 reaction equation
[CH2:1]([N:8]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:9]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]#[CH:19])=[CH:14][CH:13]=2)[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C1C=CC=CC=1.[CH2:36]([O:38][C:39](=[O:47])[C:40]1[CH:45]=[CH:44][C:43](I)=[CH:42][CH:41]=1)[CH3:37]>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>[CH2:20]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]1([C:12]2[CH:13]=[CH:14][C:15]([C:18]#[C:19][C:43]3[CH:44]=[CH:45][C:40]([C:39]([O:38][CH2:36][CH3:37])=[O:47])=[CH:41][CH:42]=3)=[CH:16][CH:17]=2)[CH2:11][CH2:10]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 2

HCID 22568868HCID 22568868, compound2×HCID 69887287Ethyl-4-iodo-benzoate benzoate2×

Product 1

HCID 22568835HCID 22568835, 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; dibenzyl-[1-(4-ethynylphenyl)-cyclopropyl]-amine (Intermediate 129, 40.0 mg, 0.12 mmol) and ethyl-4-iodo benzoate (Reagent A, 60.0 mg, 0.22 mmol) in triethylamine (5 mL) was treated with copper(I)iodide (8.0 mg, 0.04 mmol) and sparged with argon for 5 minutes. Dichlorobis (triphenylphosphine)palladium(II) (27 mg, 0.04 mmol) was added and the reaction mixture was stirred overnight at room temperature. Column chromatography (2-5% EtOAc-hexanes) afforded the title compound as an oil.

Workup

  1. customsparged with argon for 5 minutes

Sources & evidence

ORD record
ord-276eebe73b4f473a818c370602fce18e
Source dataset
uspto-grants-2004_03
Patent number
US06713647B2

Reaction notes

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