Hydrogen Bromide → 2-(5-Cyclopropyl-3-phenyl-isoxazol-4-yl)-imidazo[1,2-a]pyridine

HRID 731669노트

반응식

HRID 731669 반응식
Br[CH2:2][C:3]([C:5]1[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:7][O:8][C:9]=1[CH:10]1[CH2:12][CH2:11]1)=O.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1.Br>C(O)C>[CH:10]1([C:9]2[O:8][N:7]=[C:6]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:5]=2[C:3]2[N:19]=[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]3[CH:2]=2)[CH2:12][CH2:11]1

참가 물질

5

반응물 3

HCID 260Hydrogen BromideHCID 104392-Aminopyridine2회HCID 247398072-Bromo-1-(5-cyclopropyl-3-phenyl-isoxazol-4-yl)-ethanone

생성물 1

HCID 690683842-(5-Cyclopropyl-3-phenyl-isoxazol-4-yl)-imidazo[1,2-a]pyridine수율 54.2%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 2-bromo-1-(5-cyclopropyl-3-phenyl-isoxazol-4-yl)-ethanone (91.8mg, 0.3 mmol) and 2-aminopyridine (28.2 mg, 0.3 mmol) in ethanol (2 mL) containing hydrobromic acid (48%, 16.9 μL, 0.8 mmol) was heated under reflux under argon for 2 h. Another portion of 2-aminopyridine (28.2 mg, 0.3 mmol) was added and heating continued under reflux under argon for 1 h. After cooling to room temperature, the mixture was evaporated and poured onto saturated sodium hydrogen carbonate and extracted with ethyl acetate. The combined organic layers were then washed with water and brine, dried over sodium sulphate and evaporated to leave a yellow oil. Purification by chromatography (SiO2, heptane:ethyl acetate: 100:0 to 50:50) afforded the title compound (49 mg, 54%) which was obtained as an off-white solid. MS: m/e=302.1 [M+H]+.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux under argon for 2 h
  3. temperatureheating
  4. temperatureunder reflux under argon for 1 h
  5. customthe mixture was evaporated
  6. additionpoured onto saturated sodium hydrogen carbonate
  7. extractionextracted with ethyl acetate
  8. washThe combined organic layers were then washed with water and brine
  9. dry with materialdried over sodium sulphate
  10. customevaporated
  11. customto leave a yellow oil
  12. customPurification by chromatography (SiO2, heptane:ethyl acetate: 100:0 to 50:50)

출처 및 근거

ORD 기록
ord-f73ad2ea70054f498472de732f927c98
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585874B2

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