Triethylamine → Ethyl4-[4-(1-benzyloxycyclopropyl)-3-methyl-phenylethynyl]-benzoate

HRID 24159Notes

Reaction equation

HRID 24159 reaction equation
COC(=O)C[C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3([O:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1.[CH2:31]([O:33][C:34](=[O:42])C1C=CC(I)=CC=1)[CH3:32].[CH2:43](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>[CH2:23]([O:22][C:19]1([C:16]2[CH:15]=[CH:14][C:13]([C:12]#[C:11][C:8]3[CH:7]=[CH:6][C:5]([C:34]([O:33][CH2:31][CH3:32])=[O:42])=[CH:10][CH:9]=3)=[CH:18][C:17]=2[CH3:43])[CH2:21][CH2:20]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 142891Ethyl 4-iodobenzoate2×HCID 86585923Methyl{4-[4-(1-benzyloxycyclopropyl)-phenylethynyl]-phenyl}-acetate2×

Product 1

HCID 22568984Ethyl4-[4-(1-benzyloxycyclopropyl)-3-methyl-phenylethynyl]-benzoateYield 54%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

Using General Procedure F; 1-ethynyl-4-(1-benzyloxycyclopropyl)-3-methyl-benzene (Intermediate 76, 90.0 mg, 0.34 mmol) and ethyl-4-iodo benzoate (Reagent A, 95.0 mg, 0.34 mmol) in triethylamine (6 mL) was treated with copper(I)iodide (23.0 mg, 0.12 mmol) and sparged with argon for 5 minutes. Dichlorobis(triphenylphosphine)palladium(II) (80 mg, 0.11 mmol) was added and the reaction mixture was stirred overnight at room temperature. Column chromatography (2-4% EtOAc—hexanes) afforded 68.0 mg (54%) of the title compound.

Workup

  1. customsparged with argon for 5 minutes

Sources & evidence

ORD record
ord-1f7f83bc830648888489d31a8f102b64
Source dataset
uspto-grants-2005_02
Patent number
US06855512B2

Reaction notes

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