Iodoethane → 7-(Ethyloxy)-3-methyl-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid

HRID 245175노트

반응식

HRID 245175 반응식
I[CH2:2][CH3:3].[OH:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([C:26]([O:28]C)=[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]([CH3:33])(=[O:32])=[O:31].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C)C=O>[CH2:2]([O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([C:26]([OH:28])=[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]([CH3:33])(=[O:32])=[O:31])[CH3:3]

참가 물질

5

반응물 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 136338340Methyl 7-hydroxy-3-methyl-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate

생성물 1

HCID 674175377-(Ethyloxy)-3-methyl-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid수율 91%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Iodoethane (1.10 mL, 13.65 mL) was slowly added to a mixture of methyl 7-hydroxy-3-methyl-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (3.0 g, 6.83 mmol) and Cs2CO3 (6.67 g, 20.48 mmol) in N,N-dimethylformamide (30 mL) at room temperature. The reaction mixture was stirred overnight, quenched with saturated NH4Cl, and extracted with methylene chloride (three times). The combined organic extracts were washed with brine (two times), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified via column chromatography (ISCO, 120 g silica, 0-20% ethyl acetate/methylene chloride) to afford 7-(ethyloxy)-3-methyl-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (2.92 g, 91% yield). 1H NMR (400 MHz, DMSO-d6) δ8.25 (s, 1H), 7.98-8.06 (m, 2H), 7.92 (d, J=8.03 Hz, 1H), 7.76-7.83 (m, 2H), 4.40 (q, J=6.94 Hz, 2H), 4.09 (s, 3H), 2.37 (s, 3H), 1.47 (t, J=6.90 Hz, 3H); MS (m/z) 468.1 (M+H+).

후처리

  1. customquenched with saturated NH4Cl
  2. extractionextracted with methylene chloride (three times)
  3. washThe combined organic extracts were washed with brine (two times)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified via column chromatography (ISCO, 120 g silica, 0-20% ethyl acetate/methylene chloride)

출처 및 근거

ORD 기록
ord-5bf9ea3e742445b598fb4f799fe1cd13
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658636B2

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