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

HRID 1521673ノート

反応式

HRID 1521673 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 (157-4, 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. Then the organic phase was separated, and the water phase was extracted with ethyl acetate (5×10 mL). The combined organic phases were washed with brine, dried over Na2SO4, and evaporated under reduced pressure. The crude compound was purified by flash chromatography on silica gel to obtain title compound (white solid). 1H NMR (DMSO-D6, 500 MHz) 6=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. customThen the organic phase was 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. customevaporated under reduced pressure
  7. customThe crude compound was purified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-06a158e339df4f6eb434d5baca19c572
出典データセット
uspto-grants-2015_07
特許番号
US09073929B2

反応ノート

読み込み中…