Methyl 4-Iodophenylacetate → Methyl(4-{4-[(cyclopropyl-ethyl-amino)methyl]-3-methyl-phenylethynyl}-phenyl)-acetate

HRID 841506Notes

Reaction equation

HRID 841506 reaction equation
[CH:1]1([N:4]([CH2:15][CH3:16])[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.[CH3:17][O:18][C:19](=[O:28])[CH2:20][C:21]1[CH:26]=[CH:25][C:24](I)=[CH:23][CH:22]=1>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>[CH3:17][O:18][C:19](=[O:28])[CH2:20][C:21]1[CH:22]=[CH:23][C:24]([C:13]#[C:12][C:9]2[CH:10]=[CH:11][C:6]([CH2:5][N:4]([CH:1]3[CH2:3][CH2:2]3)[CH2:15][CH3:16])=[C:7]([CH3:14])[CH:8]=2)=[CH:25][CH:26]=1

Participants

6

Reactant 2

HCID 10378700Methyl 4-Iodophenylacetate2×HCID 22568991HCID 22568991, compound2×

Product 1

HCID 18340273Methyl(4-{4-[(cyclopropyl-ethyl-amino)methyl]-3-methyl-phenylethynyl}-phenyl)-acetateYield 53%

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; cyclopropyl-ethyl-(4-ethynyl-2-methyl-benzyl)-amine (Intermediate 161, 300.0 mg, 1.41 mmols) and methyl-(4-iodophenyl)-acetate (Reagent B, 388.0 mg, 1.41 mmols) in triethylamine (8 mL) was treated with copper(I)iodide (67.0 mg, 0.35 mmol) and sparged with argon for 15 minutes. Dichlorobis(triphenylphosphine)palladium(II) (246 mg, 0.35 mmol) was added and the reaction mixture was stirred overnight at room temperature. Column chromatography (5-7% EtOAc-hexanes) afforded 270.0 mg (53%) of the title compound as a pale-yellow oil.

Workup

  1. customsparged with argon for 15 minutes

Sources & evidence

ORD record
ord-618235339ea5442a9d87d8ccc1a0f077
Source dataset
uspto-grants-2002_04
Patent number
US06369225B1

Reaction notes

Loading…