Benzyl-[1-(4-ethynylphenyl)-cyclopropyl]-methylamine → HCID 22568953, compound

HRID 51792Notes

Reaction equation

HRID 51792 reaction equation
[CH2:1]([N:8]([C:10]1([C:13]2[CH:18]=[CH:17][C:16]([C:19]#[CH:20])=[CH:15][CH:14]=2)[CH2:12][CH2:11]1)[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C1C=CC=CC=1.[CH2:30]([O:32][C:33](=[O:41])[C:34]1[CH:39]=[CH:38][C:37](I)=[CH:36][CH:35]=1)[CH3:31]>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]([N:8]([CH3:9])[C:10]1([C:13]2[CH:14]=[CH:15][C:16]([C:19]#[C:20][C:37]3[CH:38]=[CH:39][C:34]([C:33]([O:32][CH2:30][CH3:31])=[O:41])=[CH:35][CH:36]=3)=[CH:17][CH:18]=2)[CH2:12][CH2:11]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 22568949Benzyl-[1-(4-ethynylphenyl)-cyclopropyl]-methylamine2×HCID 69887287Ethyl-4-iodo-benzoate benzoate2×

Product 1

HCID 22568953HCID 22568953, compoundYield 75%

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; benzyl-[1-(4-ethynylphenyl)-cyclopropyl]-methylamine (Intermediate 132, 70.0 mg, 0.28 mmol) and ethyl-4-iodo benzoate (Reagent A, 77.0 mg, 0.28 mmol) in triethylamine (5 mL) was treated with copper(I)iodide (18.0 mg, 0.10 mmol) and sparged with argon for 5 minutes. Dichlorobis (triphenylphosphine)palladium(II) (65 mg, 0.10 mmol) was added and the reaction mixture was stirred overnight at room temperature. Column chromatography (2-5% EtOAc-hexanes) afforded 86 mg (75%) of the title compound as an oil.

Workup

  1. customsparged with argon for 5 minutes

Sources & evidence

ORD record
ord-1cbe6f9096034dca88f079642785b8a9
Source dataset
uspto-grants-2004_03
Patent number
US06713647B2

Reaction notes

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