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

HRID 76201
ノート
印刷プレビュー

反応式

HRID 76201 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-07cc6972bbba45a1a6b1aa91f33e7fcd
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08835472B2

反応ノート

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