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

HRID 245241노트

반응식

HRID 245241 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
120 °C

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-19ba3ca096b34b5d85b82c89bc1bbdce
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658636B2

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