Triethylamine → Ethyl4-[4-[1-(2,2-dimethylpropyloxy)-cyclopropyl]-3-methyl-phenylethynyl]-benzoate

HRID 381091Notes

Reaction equation

HRID 381091 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2([O:12][CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:11][CH2:10]2)=[CH:5][C:4]=1C)#[CH:2].[CH2:19]([O:21][C:22](=[O:30])[C:23]1[CH:28]=[CH:27][C:26](I)=[CH:25][CH:24]=1)[CH3:20].[CH2:31](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>[CH2:19]([O:21][C:22](=[O:30])[C:23]1[CH:28]=[CH:27][C:26]([C:2]#[C:1][C:3]2[CH:4]=[CH:5][C:6]([C:9]3([O:12][CH2:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:10][CH2:11]3)=[C:7]([CH3:31])[CH:8]=2)=[CH:25][CH:24]=1)[CH3:20]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 142891Ethyl 4-iodobenzoate2×HCID 225690224-Ethynyl-1-[1-(2,2-dimethylpropyloxy)-cyclopropyl]3-methyl-benzene2×

Product 1

HCID 22568999Ethyl4-[4-[1-(2,2-dimethylpropyloxy)-cyclopropyl]-3-methyl-phenylethynyl]-benzoateYield 50%

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; 4-ethynyl-1-[1-(2,2-dimethylpropyloxy)-cyclopropyl]-3-methyl-benzene (Intermediate 85, 75.0 mg, 0.31 mmol) and ethyl-4-iodo benzoate (Reagent A, 86.0 mg, 0.31 mmol) in triethylamine (5 mL) was treated with copper(I)iodide (21.0 mg, 0.11 mmol) and sparged with argon for 5 minutes. Dichlorobis(triphenylphosphine)-palladium(II) (78 mg, 0.11 mmol) was added and the reaction mixture was stirred overnight at room temperature. Column chromatography (2-4% EtOAc-hexanes) afforded 60.0 mg (50%) of the title compound as an orange solid.

Workup

  1. customsparged with argon for 5 minutes

Sources & evidence

ORD record
ord-18731f27e8e54de9b1d4dd1d916b512c
Source dataset
uspto-grants-2001_10
Patent number
US06303785B1

Reaction notes

Loading…