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

HRID 1617816ノート

反応式

HRID 1617816 の反応式
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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8082Piperidine溶媒

反応条件

温度
50 °C

実験手順

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]+).

後処理

  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)

出典と根拠

ORDレコード
ord-5c28b3fd283346ceb6918a632bc05304
出典データセット
uspto-grants-2014_07
特許番号
US08765730B2

反応ノート

読み込み中…