Water → N-benzyl-N-[2-(2-methoxy-5-trimethylsilanylethynyl-pyridin-3-yl)-5-trifluoromethyl-benzyl]-acetamide

HRID 554645ノート

反応式

HRID 554645 の反応式
[CH2:1]([N:8]([CH2:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:14]=1[C:23]1[C:24]([O:30][CH3:31])=[N:25][CH:26]=[C:27](Br)[CH:28]=1)[C:9](=[O:11])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:32][Si:33]([C:36]#[CH:37])([CH3:35])[CH3:34].C(Cl)Cl.O>C(N(CC)CC)C.CN(C=O)C.[Cu](I)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>[CH2:1]([N:8]([CH2:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:14]=1[C:23]1[C:24]([O:30][CH3:31])=[N:25][CH:26]=[C:27]([C:37]#[C:36][Si:33]([CH3:35])([CH3:34])[CH3:32])[CH:28]=1)[C:9](=[O:11])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

9

反応物 4

HCID 962WaterHCID 6344DichloromethaneHCID 66111TrimethylsilylacetyleneHCID 67212466N-benzyl-N-[2-(5-bromo-2-methoxy-pyridin-3-yl)-5-trifluoromethyl-benzyl]-acetamide

生成物 1

HCID 67212387N-benzyl-N-[2-(2-methoxy-5-trimethylsilanylethynyl-pyridin-3-yl)-5-trifluoromethyl-benzyl]-acetamide

試薬・触媒・溶媒 4

HCID 6228Dimethylformamide触媒HCID 83717Copper iodide触媒HCID 178418476HCID 178418476、化合物触媒HCID 8471Triethylamine溶媒

実験手順

N-Benzyl-N-[2-(5-bromo-2-methoxy-pyridin-3-yl)-5-trifluoromethyl-benzyl]-acetamide (0.288 g, 0.58 mmol), (trimethylsilyl)acetylene (0.08 mL, 0.58 mmol), and copper iodide (0.011 g, 0.06 mmol) were combined in triethylamine (3.5 mL), and the solution was purged with N2 for 25 minutes. Dichlorobis(triphenylphosphine)palladium(II) (0.042 g, 0.06 mmol) was added, and the reaction was stirred at room temperature overnight. A few drops of DMF was added, and the reaction was stirred at 50° C. for 5 hours, and at 60° C. for 3 hours. The mixture was worked-up with CH2Cl2 and H2O, and the combined organic layers were dried, filtered, and concentrated. The residue was purified by silica gel chromatography (0-30% EtOAc in hexanes) to give N-benzyl-N-[2-(2-methoxy-5-trimethylsilanylethynyl-pyridin-3-yl)-5-trifluoromethyl-benzyl]-acetamide.

後処理

  1. customthe solution was purged with N2 for 25 minutes
  2. stirringthe reaction was stirred at 50° C. for 5 hours
  3. waitat 60° C. for 3 hours
  4. customthe combined organic layers were dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (0-30% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-a93728d588944735a3b8462e31acaa8e
出典データセット
uspto-grants-2011_11
特許番号
US08049015B2

反応ノート

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