HCID 22568991, compound → HCID 22568859, compound

HRID 51821Notes

Reaction equation

HRID 51821 reaction equation
[CH:1]1([N:4]([CH2:15][CH3:16])[CH2:5][C:6]2[CH:11]=[CH:10][C:9]([C:12]#[CH:13])=[CH:8][C:7]=2[CH3:14])[CH2:3][CH2:2]1.C(O)(=O)C1C=CC=CC=1.[CH2:26]([O:28][C:29](=[O:37])[C:30]1[CH:35]=[CH:34][C:33](I)=[CH:32][CH:31]=1)[CH3:27]>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>[CH:1]1([N:4]([CH2:5][C:6]2[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:33]3[CH:34]=[CH:35][C:30]([C:29]([O:28][CH2:26][CH3:27])=[O:37])=[CH:31][CH:32]=3)=[CH:8][C:7]=2[CH3:14])[CH2:15][CH3:16])[CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 22568991HCID 22568991, compound2×HCID 69887287Ethyl-4-iodo-benzoate benzoate2×

Product 1

HCID 22568859HCID 22568859, 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; cyclopropyl-ethyl-(4-ethynyl-2-methyl-benzyl)-amine (Intermediate 161, 190.0 mg, 0.89 mmol) and ethyl-4-iodo benzoate (Reagent A, 245.0 mg, 0.89 mmol) in triethylamine (5 mL) was treated with copper(I)iodide (56.0 mg, 0.30 mmol) and sparged with argon for 15 minutes. Dichlorobis(triphenylphosphine)-palladium(II) (208 mg, 0.30 mmol) was added and the reaction mixture was stirred overnight at room temperature. Column chromatography (3-5% EtOAc-hexanes) afforded the title compound.

Workup

  1. customsparged with argon for 15 minutes

Sources & evidence

ORD record
ord-d726e96b66a94536aa6997dd48bcdd7e
Source dataset
uspto-grants-2004_03
Patent number
US06713647B2

Reaction notes

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