Water → (R)-1-(2-Methyl-pyridin-4-yl)-3-o-tolyl-3-(4-trimethylsilanylethynyl-phenyl)-propan-1-one

HRID 1617816노트

반응식

HRID 1617816 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:25])[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([CH3:18])[CH:13]=2)=[O:11])=[CH:4][CH:3]=1.[C:26]([Si:28]([CH3:31])([CH3:30])[CH3:29])#[CH:27].O.COC(C)(C)C>N1CCCCC1>[CH3:18][C:14]1[CH:13]=[C:12]([C:10](=[O:11])[CH2:9][C@@H:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:25])[C:5]2[CH:6]=[CH:7][C:2]([C:27]#[C:26][Si:28]([CH3:31])([CH3:30])[CH3:29])=[CH:3][CH:4]=2)[CH:17]=[CH:16][N:15]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 15413tert-Butyl methyl etherHCID 66111TrimethylsilylacetyleneHCID 66666695(R)-3-(4-Bromo-phenyl)-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one

생성물 1

HCID 67015635(R)-1-(2-Methyl-pyridin-4-yl)-3-o-tolyl-3-(4-trimethylsilanylethynyl-phenyl)-propan-1-one수율 61%

시약·촉매·용매 1

HCID 8082Piperidine용매

반응 조건

온도
50 °C

실험 절차

To a solution of (R)-3-(4-bromo-phenyl)-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one (example 142, step 2, 150 mg) in piperidine (3 mL) were added under argon copper(I) iodide (3.6 mg) and tetrakis-triphenylphosphine palladium(0) (22 mg). The reaction mixture was heated at 50° C. and ethynyltrimethylsilane (480 μL) was added. The reaction mixture was stirred at 50° C. overnight. water and tert-butyl methyl ether were added, the phases were separated and the inorganic one was extracted with tert-butyl methyl ether (2×). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (15% to 50% ethyl acetate in n-heptane) to yield the title compound as a light yellow oil (105 mg, 61%), MS (ESI+): m/z=412.4 ([M+H]+).

후처리

  1. customthe phases were separated
  2. extractionthe inorganic one was extracted with tert-butyl methyl ether (2×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography on silica gel (15% to 50% ethyl acetate in n-heptane)

출처 및 근거

ORD 기록
ord-5c28b3fd283346ceb6918a632bc05304
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765730B2

반응 노트

불러오는 중…