Triethylamine → 4-Ethynyl-1-(1-benzyloxycyclopropyl)-2-methyl-benzene

HRID 1935863Notes

Reaction equation

HRID 1935863 reaction equation
[CH2:1]([O:8][C:9]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]#CC3C=CC(CC(OC)=O)=CC=3)=[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(OC(=O)C1C=CC(I)=CC=1)C.C(N([CH2:48][CH3:49])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>[C:16]([C:15]1[CH:14]=[CH:13][C:12]([C:9]2([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:11][CH2:10]2)=[C:48]([CH3:49])[CH:18]=1)#[CH:17]

Participants

6

Reactant 3

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

Product 1

HCID 225688524-Ethynyl-1-(1-benzyloxycyclopropyl)-2-methyl-benzeneYield 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-c7eb16dc7e0d4122b2771a2f7c0e915f
Source dataset
uspto-grants-2002_05
Patent number
US06387892B1

Reaction notes

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