Iodoethane → Methyl 7-(ethyloxy)-3-methyl-6-[(1-methylethyl)sulfonyl]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate

HRID 245205노트

반응식

HRID 245205 반응식
I[CH2:2][CH3:3].[OH:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([C:26]([O:28][CH3:29])=[O:27])=[C:10]([CH3:25])[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=3)=[N:12]2)=[CH:7][C:6]=1[S:30]([CH:33]([CH3:35])[CH3:34])(=[O:32])=[O:31].C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.O>[CH2:2]([O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([C:26]([O:28][CH3:29])=[O:27])=[C:10]([CH3:25])[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:23])([F:24])[F:22])[CH:16]=3)=[N:12]2)=[CH:7][C:6]=1[S:30]([CH:33]([CH3:35])[CH3:34])(=[O:32])=[O:31])[CH3:3]

참가 물질

6

반응물 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 136338326Methyl 7-hydroxy-3-methyl-6-[(1-methylethyl)sulfonyl]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate

생성물 1

HCID 67383983Methyl 7-(ethyloxy)-3-methyl-6-[(1-methylethyl)sulfonyl]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate수율 83.3%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

Iodoethane (3.35 mL, 41.4 mmol) was added slowly to a mixture of methyl 7-hydroxy-3-methyl-6-[(1-methylethyl)sulfonyl]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (12.90 g, 27.6 mmol) and cesium carbonate (27.0 g, 83 mmol) in dimethyl sulfoxide (150 mL) at room temperature. The mixture was stirred at room temperature overnight. The mixture was diluted with water and extracted with methylene chloride. The phases were separated, and the organic phase was washed with brine, dried over Na2SO4, filtered, and concentrated. The crude material was purified via column chromatography (ISCO, 330 g silica, 0-20% ethyl acetate/methylene chloride) to afford a solid residue that was triturated from methanol to give methyl 7-(ethyloxy)-3-methyl-6-[(1-methylethyl)sulfonyl]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (11.39 g, 83% yield). 1H NMR (400 MHz, DMSO-d6) δ8.24 (s, 1H), 7.98-8.04 (m, 2H), 7.91 (d, J=7.78 Hz, 1H), 7.76-7.82 (m, 2H), 4.39 (q, J=7.03 Hz, 2H), 4.09 (s, 3H), 3.85 (quin, J=6.84 Hz, 1H), 2.36 (s, 3H), 1.44 (t, J=7.03 Hz, 3H), 1.23 (s, 3H), 1.21 (s, 3H); MS (m/z) 496.1 (M+H+).

후처리

  1. extractionextracted with methylene chloride
  2. customThe phases were separated
  3. washthe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified via column chromatography (ISCO, 330 g silica, 0-20% ethyl acetate/methylene chloride)
  8. customto afford a solid residue that
  9. customwas triturated from methanol

출처 및 근거

ORD 기록
ord-49a1d150138543af9d1c99d1468f9a25
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658636B2

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