Water → N-(1-(4-((4-Chlorophenyl)ethynyl)phenyl)propan-2-yl)acetamide

HRID 76183

Reaction equation

HRID 76183 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([NH:11][C:12](=[O:14])[CH3:13])[CH3:10])=[CH:4][CH:3]=1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]#[CH:23])=[CH:18][CH:17]=1.O>C(N)(CC)C.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>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]#[C:23][C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([NH:11][C:12](=[O:14])[CH3:13])[CH3:10])=[CH:4][CH:3]=2)=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 962WaterHCID 70118Benzene, 1-chloro-4-ethynyl-HCID 66611344N-(1-(4-Iodophenyl)propan-2-YL)acetamide

Product 1

HCID 56924958N-(1-(4-((4-Chlorophenyl)ethynyl)phenyl)propan-2-yl)acetamide

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 24874Sec-ButylamineSolvent

Procedure

To 45.5 mg (0.15 mmol) N-(1-(4-iodophenyl)propan-2-yl)acetamide (I52.1) and 27.3 mg (0.20 mmol) 1-chloro-4-ethynylbenzene in 750 μl sec-butylamine are added 14.3 (0.02 mmol) bis(triphenyphosphine)dichloropalladium (in 400 μl sec-butylamine) followed by 1.0 mL water. The reaction mixture is stirred at r.t. overnight. The solvent is removed in vacuo and the residue is purified by HPLC (ACN/H2O/TFA).

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is purified by HPLC (ACN/H2O/TFA)

Sources & evidence

ORD record
ord-7ab3636260214442aeb49d5e398ff055
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Linked notes

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