[1-(4-Ethynylphenyl)-cyclopropyl]-propylamine → Ethyl4-[4-(1-propylamino-cyclopropyl)-phenylethynyl]-benzoate

HRID 51774Notes

Reaction equation

HRID 51774 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2([NH:12][CH2:13][CH2:14][CH3:15])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[CH:2].C(O)(=O)C1C=CC=CC=1.[CH2:25]([O:27][C:28](=[O:36])[C:29]1[CH:34]=[CH:33][C:32](I)=[CH:31][CH:30]=1)[CH3:26]>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>[CH2:13]([NH:12][C:9]1([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[C:2][C:32]3[CH:33]=[CH:34][C:29]([C:28]([O:27][CH2:25][CH3:26])=[O:36])=[CH:30][CH:31]=3)=[CH:4][CH:5]=2)[CH2:10][CH2:11]1)[CH2:14][CH3:15]

Participants

6

Reactant 2

HCID 22568926[1-(4-Ethynylphenyl)-cyclopropyl]-propylamine2×HCID 69887287Ethyl-4-iodo-benzoate benzoate2×

Product 1

HCID 22568896Ethyl4-[4-(1-propylamino-cyclopropyl)-phenylethynyl]-benzoateYield 61%

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]-propylamine (Intermediate 120, 38.0 mg, 0.19 mmol) and ethyl-4-iodo benzoate (Reagent A, 58.0 mg, 0.21 mmol) in triethyl amine (6 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 (5-15% EtOAc-hexanes) afforded 40.0 mg (61%) of the title compound as an orange oil.

Workup

  1. customsparged with argon for 5 minutes

Sources & evidence

ORD record
ord-4db0ca36a11940c8b06cd426f8995d4a
Source dataset
uspto-grants-2004_03
Patent number
US06713647B2

Reaction notes

Loading…