Triethylamine → HCID 131722891, compound

HRID 381158Notes

Reaction equation

HRID 381158 reaction equation
[CH:1]1([N:4](CC)[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.[CH2:17]([O:19][C:20](=[O:28])[C:21]1[CH:26]=[CH:25][C:24](I)=[CH:23][CH:22]=1)[CH3:18].[CH2:29](N(CC)CC)[CH3:30]>[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>[CH2:17]([O:19][C:20](=[O:28])[C:21]1[CH:26]=[CH:25][C:24]([C:13]#[C:12][C:9]2[CH:10]=[CH:11][C:6]([CH2:5][NH:4][CH2:1][CH:3]=[C:2]3[CH2:30][CH2:29]3)=[C:7]([CH3:14])[CH:8]=2)=[CH:23][CH:22]=1)[CH3:18]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 142891Ethyl 4-iodobenzoate2×HCID 22568991HCID 22568991, compound2×

Product 1

HCID 131722891HCID 131722891, compound

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; 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-0feceff05e37498bb49c3cbe51bd4423
Source dataset
uspto-grants-2001_10
Patent number
US06303785B1

Reaction notes

Loading…