2-Amino-3-benzyloxypyridine → 8-Benzyloxy-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine

HRID 4300

반응식

HRID 4300 반응식
[NH2:1][C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.S(OC(CC#C)C(=O)C)([C:19]1[CH:25]=[CH:24][C:22](C)=[CH:21][CH:20]=1)(=O)=O>C(O)C>[CH2:9]([O:8][C:7]1[C:2]2[N:3]([C:19]([CH2:20][C:21]#[CH:22])=[C:25]([CH3:24])[N:1]=2)[CH:4]=[CH:5][CH:6]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

참가 물질

4

반응물 2

HCID 903342-Amino-3-benzyloxypyridineHCID 138258933-Tosyloxy-5-hexyn-2-one

생성물 1

HCID 138258978-Benzyloxy-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine수율 31%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of 2-amino-3-benzyloxypyridine (2 g) and 3-tosyloxy-5-hexyn-2-one (2.66 g) in ethanol (15 ml) was stirred and refluxed for 24 hours and then evaporated in vacuo. To the residue was added an aqueous solution of sodium bicarbonate and the mixture was extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and evaporated in vacuo. The oily residue was purified by column chromatography on silica gel (50 g) using chloroform as an eluent to give a solid, which was recrystallized from a mixture of methylene chloride and diethyl ether to give 8-benzyloxy-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine (0.855 g).

후처리

  1. temperaturerefluxed for 24 hours
  2. customevaporated in vacuo
  3. additionTo the residue was added an aqueous solution of sodium bicarbonate
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe oily residue was purified by column chromatography on silica gel (50 g)
  9. customto give a solid, which
  10. customwas recrystallized from a mixture of methylene chloride and diethyl ether

출처 및 근거

ORD 기록
ord-30e0a8c847e3408db73ba26ed7bed814
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04725601

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