Ethyl 4-iodobenzoate → HCID 22568957, compound

HRID 1935919Notes

Reaction equation

HRID 1935919 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2([N:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[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]>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>[CH2:13]([N:12]([CH2:16][CH2:17][CH3:18])[C:9]1([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[C:2][C:26]3[CH:27]=[CH:28][C:23]([C:22]([O:21][CH2:19][CH3:20])=[O:30])=[CH:24][CH:25]=3)=[CH:4][CH:5]=2)[CH2:10][CH2:11]1)[CH2:14][CH3:15]

Participants

6

Reactant 2

HCID 142891Ethyl 4-iodobenzoate2×HCID 225689121-(4-Ethynylphenyl)-cyclopropyl-dipropylamine2×

Product 1

HCID 22568957HCID 22568957, 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; [1-(4-ethynylphenyl)-cyclopropyl]-dipropylamine (Intermediate 123, 34.0 mg, 0.16 mmol) and ethyl-4-iodo benzoate (Reagent A, 59.0 mg, 0.21 mmol) in triethyl amine (6 mL) was treated with copper(I)iodide (13.0 mg, 0.07 mmol) and sparged with argon for 5 minutes. Dichlorobis(triphenylphosphine)palladium(II) (49 mg, 0.07 mmol) was added and the reaction mixture was stirred overnight at room temperature. Column chromatography (2-4% EtOAc-hexanes) afforded the title compound as a yellow oil.

Workup

  1. customsparged with argon for 5 minutes

Sources & evidence

ORD record
ord-73c68e45638348c2a3ac5d2366985e7d
Source dataset
uspto-grants-2002_05
Patent number
US06387892B1

Reaction notes

Loading…