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

HRID 841506
Notes
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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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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)Catalyst
HCID 178418476
HCID 178418476, compound
Catalyst
HCID 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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06369225B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes