Sodium methanesulfinate → Methyl 3-methyl-6-(methylsulfonyl)-2-[4-(trifluoromethyl)phenyl]-4-quinolinecarboxylate

HRID 245241ノート

反応式

HRID 245241 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=1)[C:6]([CH3:22])=[C:5]2[C:23]([O:25][CH3:26])=[O:24].[Na+].[CH3:28][S:29]([O-:31])=[O:30]>CS(C)=O.[Cu]I>[CH3:22][C:6]1[C:7]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)=[N:8][C:9]2[C:4]([C:5]=1[C:23]([O:25][CH3:26])=[O:24])=[CH:3][C:2]([S:29]([CH3:28])(=[O:31])=[O:30])=[CH:11][CH:10]=2

参加物

5

反応物 2

HCID 2733271Sodium methanesulfinateHCID 67384046Methyl 6-bromo-3-methyl-2-[4-(trifluoromethyl)phenyl]-4-quinolinecarboxylate

生成物 1

HCID 67384122Methyl 3-methyl-6-(methylsulfonyl)-2-[4-(trifluoromethyl)phenyl]-4-quinolinecarboxylate

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
120 °C

実験手順

Methyl 6-bromo-3-methyl-2-[4-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (5.1 g, 12.02 mmol) was dissolved in dimethyl sulfoxide (60 mL) and copper(I) iodide (4.58 g, 24.04 mmol) and methanesulfinic acid sodium salt (2.455 g, 24.04 mmol) were added. The reaction vessel was evacuated and flushed with N2 three times, and heated at 120° C. overnight. The reaction mixture was diluted with CH2Cl2 and H2O, stirred for 30 min, filtered through the Celite, and washed with CH2Cl2. The filtrate was extracted three times with CH2Cl2, and the combined organic extracts were washed twice with brine, and dried over Na2SO4. The residue was purified via silica gel flash chromatography (0%-20% EtOAc/CH2Cl2) to afford the desired product as an off white solid (3.3 g, 65%). MS (m/z) 424.0 (M+H+).

後処理

  1. customThe reaction vessel was evacuated
  2. customflushed with N2 three times
  3. additionThe reaction mixture was diluted with CH2Cl2 and H2O
  4. filtrationfiltered through the Celite
  5. washwashed with CH2Cl2
  6. extractionThe filtrate was extracted three times with CH2Cl2
  7. washthe combined organic extracts were washed twice with brine
  8. dry with materialdried over Na2SO4
  9. customThe residue was purified via silica gel flash chromatography (0%-20% EtOAc/CH2Cl2)

出典と根拠

ORDレコード
ord-19ba3ca096b34b5d85b82c89bc1bbdce
出典データセット
uspto-grants-2014_02
特許番号
US08658636B2

反応ノート

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