Piperidine → N-(1-(4-((2,4-Dimethoxyphenyl)ethynyl)phenyl)propan-2-yl)acetamide

HRID 76184

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([NH:12][C:13](=[O:15])[CH3:14])[CH3:11])=[CH:5][CH:4]=1)#[CH:2].Br[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=1[O:25][CH3:26].N1CCCCC1>CC(C)=O.O.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>[CH3:24][O:23][C:20]1[CH:19]=[C:18]([O:25][CH3:26])[CH:17]=[CH:22][C:21]=1[C:2]#[C:1][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([NH:12][C:13](=[O:15])[CH3:14])[CH3:11])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 36.2 mg (0.18 mmol) N-(1-(4-ethynylphenyl)propan-2-yl)acetamide (I58.3) and 300 μl acetone is added to 50.6 mg (0.15 mmol) 1-bromo-2,4-dimethoxybenzene followed by a suspension of 14.3 (0.02 mmol) bis(triphenylphosphine)dichloropalladium in 300 μl acetone and 600 μl water. After addition of 22.4 mg (0.20 mmol) piperidine the mixture is stirred in a sealed tube for 1.5 h at 60° C. The solvent is removed in vacuo and the residue is purified by HPLC (ACN/H2O/TFA).

Workup

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

Sources & evidence

ORD record: ord-27c461a59245463c8a25427a17c3c608
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835472B2

Linked notes

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