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

HRID 554645노트

반응식

HRID 554645 반응식
[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

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 6228Dimethylformamide촉매HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8471Triethylamine용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-a93728d588944735a3b8462e31acaa8e
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08049015B2

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