Trimethylsilylacetylene → 2,2,2-Trifluoro-N-{2-(methyloxy)-5[(trimethylsilyl)ethynyl]phenyl}-acetamide

HRID 1160003노트

반응식

HRID 1160003 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([O:15][CH3:16])=[C:6]([NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])[CH:7]=1.[CH3:17][Si:18]([C:21]#[CH:22])([CH3:20])[CH3:19]>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.C1COCC1>[F:11][C:10]([F:13])([F:12])[C:9]([NH:8][C:6]1[CH:7]=[C:2]([C:22]#[C:21][Si:18]([CH3:20])([CH3:19])[CH3:17])[CH:3]=[CH:4][C:5]=1[O:15][CH3:16])=[O:14]

참가 물질

5

반응물 2

HCID 66111TrimethylsilylacetyleneHCID 22636844N-[5-bromo-2-(methyloxy)phenyl]-2,2,2-trifluoroacetamide

생성물 1

HCID 595114262,2,2-Trifluoro-N-{2-(methyloxy)-5[(trimethylsilyl)ethynyl]phenyl}-acetamide수율 43.1%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

To an oven-dried flask under N2 was added N-[5-bromo-2-(methyloxy)phenyl]-2,2,2-trifluoroacetamide (1.53 g, 0.005 mol), anhydrous degassed THF (100 mL), dichlorobis(triphenylphosphine)palladium(II) (0.45 g, 0.0006 mol), Cu(I)I (73 mg, 0.38 mmol), and trimethylsilylacetylene (1.26 g, 0.013 mol). Next, TEA (5.19 g, 0.05 mol) was added dropwise and the resulting mixture was heated at 60° C. overnight. The crude reaction mixture was adsorbed to silica gel and purified by column chromatography (0-10% EtOAc in hexanes) to afford the desired product (0.68 g, 42%) as an off white solid. ESIMS (M−H)−=314.

후처리

  1. customThe crude reaction mixture
  2. custompurified by column chromatography (0-10% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-581112a9c3a046d39a63cf2e42f65cd1
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812022B2

반응 노트

불러오는 중…