Water → Cyclopropanecarboxylic acid ethyl-[2-(2-methoxy-5-trimethylsilanylethynyl-pyridin-3-yl)-5-trifluoromethyl-benzyl]-amide

HRID 554617노트

반응식

HRID 554617 반응식
Br[C:2]1[CH:3]=[C:4]([C:10]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][C:11]=2[CH2:12][N:13]([CH2:19][CH3:20])[C:14]([CH:16]2[CH2:18][CH2:17]2)=[O:15])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[CH3:29][Si:30]([C:33]#[CH:34])([CH3:32])[CH3:31].C(Cl)Cl.O>C(N(CC)CC)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>[CH2:19]([N:13]([CH2:12][C:11]1[CH:21]=[C:22]([C:25]([F:28])([F:27])[F:26])[CH:23]=[CH:24][C:10]=1[C:4]1[C:5]([O:8][CH3:9])=[N:6][CH:7]=[C:2]([C:34]#[C:33][Si:30]([CH3:32])([CH3:31])[CH3:29])[CH:3]=1)[C:14]([CH:16]1[CH2:18][CH2:17]1)=[O:15])[CH3:20]

참가 물질

8

반응물 4

HCID 962WaterHCID 6344DichloromethaneHCID 66111TrimethylsilylacetyleneHCID 67212469Cyclopropanecarboxylic acid [2-(5-bromo-2-methoxy-pyridin-3-yl)-5-trifluoromethyl-benzyl]-ethyl-amide

생성물 1

HCID 67212431Cyclopropanecarboxylic acid ethyl-[2-(2-methoxy-5-trimethylsilanylethynyl-pyridin-3-yl)-5-trifluoromethyl-benzyl]-amide

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8471Triethylamine용매

실험 절차

Cyclopropanecarboxylic acid [2-(5-bromo-2-methoxy-pyridin-3-yl)-5-trifluoromethyl-benzyl]-ethyl-amide (0.215 g, 0.47 mmol), (trimethylsilyl)acetylene (0.07 mL, 0.47 mmol), and copper iodide (0.012 g, 0.05 mmol) were combined in triethylamine (2 mL), and the solution was purged with N2 for 25 minutes. Dichlorobis(triphenylphosphine)palladium(II) (0.039 g, 0.05 mmol) was added, and the reaction was stirred at room temperature overnight. 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 (0-100% EtOAc in hexanes) to give cyclopropanecarboxylic acid ethyl-[2-(2-methoxy-5-trimethylsilanylethynyl-pyridin-3-yl)-5-trifluoromethyl-benzyl]-amide.

후처리

  1. customthe solution was purged with N2 for 25 minutes
  2. customthe combined organic layers were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (0-100% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-1a16ae84a6cb4c518fb12ce9d2b61434
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08049015B2

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