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1-Ethynyl-4-propoxybenzene → N-{1-Methyl-2-[4-(4-propoxy-phenylethynyl)-phenyl]-ethyl}-acetamide

HRID 76201
Notes
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Reaction equation

HRID 76201 reaction equation
[C:1]([NH:4][CH:5]([CH3:21])[CH2:6][C:7]1[CH:12]=[CH:11][C:10](OS(C(F)(F)F)(=O)=O)=[CH:9][CH:8]=1)(=[O:3])[CH3:2].[C:22]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][CH3:33])=[CH:26][CH:25]=1)#[CH:23]>CN(C=O)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>[CH3:21][CH:5]([NH:4][C:1](=[O:3])[CH3:2])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:23]#[C:22][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][CH3:33])=[CH:26][CH:25]=2)=[CH:9][CH:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 27751231-Ethynyl-4-propoxybenzeneHCID 86669624Trifluoromethanesulfonic acid 4-(2-acetylamino-propyl)-phenyl ester

Product 1

HCID 66613508N-{1-Methyl-2-[4-(4-propoxy-phenylethynyl)-phenyl]-ethyl}-acetamide

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
80 °C

Procedure

To 0.33 g (1.00 mmol) trifluoromethanesulfonic acid 4-(2-acetylamino-propyl)-phenyl ester (I53.2) and 0.18 g (1.10 mmol) 1-ethynyl-4-propoxybenzene in 3 mL DMF and 0.60 mL (4.50 mmol) TEA are added 0.04 g (0.06 mmol) bis-(triphenylphosphin)-palladiumdichlorid. The mixture is stirred in a sealed tube at 80° C. for 24 h. The reaction mixture is partitioned between EtOAc and water, the organic layer is dried with Na2SO4 and the solvent is removed in vacuo. The residue is purified by column chromatographie (silica gel, DCM/EtOAc 1/1). The resulting product is triturated with diethylether and dried at 80° C. in vacuo.

Workup

  1. customThe reaction mixture is partitioned between EtOAc and water
  2. dry with materialthe organic layer is dried with Na2SO4
  3. customthe solvent is removed in vacuo
  4. customThe residue is purified by column chromatographie (silica gel, DCM/EtOAc 1/1)
  5. customThe resulting product is triturated with diethylether
  6. customdried at 80° C. in vacuo

Sources & evidence

ORD record
ord-07cc6972bbba45a1a6b1aa91f33e7fcd
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08835472B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes