Water → 7-Bromo-9-fluoro-1-methyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline

HRID 921970ノート

反応式

HRID 921970 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[NH:8][C:7](=S)[CH2:6][CH2:5]2.[C:14]([NH:17][NH2:18])(=O)[CH3:15].C(OCC)(=O)C.O>C(O)CCC>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[N:8]1[C:14]([CH3:15])=[N:17][N:18]=[C:7]1[CH2:6][CH2:5]2

参加物

6

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14039AcetohydrazideHCID 891560716-bromo-8-fluoro-3,4-dihydroquinoline-2(1H)-thione

生成物 1

HCID 709780527-Bromo-9-fluoro-1-methyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

実験手順

A suspension of 6-bromo-8-fluoro-3,4-dihydroquinoline-2(1H)-thione (1-4, 1.71 g, 6.57 mmol) and acetohydrazide (0.58 g, 7.89 mmol) in n-butanol (7 mL) was refluxed for 18 h under inert atmosphere. After cooling down to ambient temperature, ethyl acetate (10 mL) and water (10 mL) were added. The organic phase was then separated and the water phase was extracted with ethyl acetate (5×10 mL). The combined organic phases were washed with brine and dried over Na2SO4; the combined organic layers were then evaporated under reduced pressure to yield the crude product. The crude compound was purified by flash chromatography on silica gel to obtain the title compound as a white solid; 1H NMR (DMSO-D6, 500 MHz) δ=7.79 (dd, J=2.0 Hz, JHF=11.0 Hz, 1H), 7.63 (s, 1H), 2.95 (br s, 4H), 2.46 (d, JHF=8.5 Hz, 3H).

後処理

  1. temperaturewas refluxed for 18 h under inert atmosphere
  2. customThe organic phase was then separated
  3. extractionthe water phase was extracted with ethyl acetate (5×10 mL)
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over Na2SO4
  6. customthe combined organic layers were then evaporated under reduced pressure
  7. customto yield the crude product
  8. customThe crude compound was purified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-3576f3ab146a4661a64e6d4b9fc44f9f
出典データセット
uspto-grants-2016_03
特許番号
US09278093B2

反応ノート

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