2-Amino-3-methoxymethoxypyridine → 8-Hydroxy-2-methyl-3-(2-propynyl)imidazo[1,2-a]pyridine

HRID 2231199ノート

反応式

HRID 2231199 の反応式
[NH2:1][C:2]1[C:7]([O:8]COC)=[CH:6][CH:5]=[CH:4][N:3]=1.S(O[CH:17]([CH2:21][C:22]#[CH:23])[C:18](=O)[CH3:19])(C)(=O)=O>C(O)C>[OH:8][C:7]1[C:2]2[N:3]([C:17]([CH2:21][C:22]#[CH:23])=[C:18]([CH3:19])[N:1]=2)[CH:4]=[CH:5][CH:6]=1

参加物

4

反応物 2

HCID 143683452-Amino-3-methoxymethoxypyridineHCID 143683463-Mesyloxy-5-hexyn-2-one

生成物 1

HCID 143683478-Hydroxy-2-methyl-3-(2-propynyl)imidazo[1,2-a]pyridine収率 21.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of 2-amino-3-methoxymethoxypyridine (7.5 g) and 3-mesyloxy-5-hexyn-2-one (10.18 g), in ethanol (150 ml) was refluxed for 46.5 hours and then evaporated in vacuo. To the residue was added 20% sulfuric acid (75 ml) and the mixture was stirred for 5 hours at room temperature. The mixture was made alkaline with sodium bicarbonate and extracted with chloroform. The extract was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel (30 g) with chloroform and then a mixture of chloroform and methanol (30:1 to 20:1) as eluents. The eluates were evaporated in vacuo and the residue was recrystallized from a mixture of ethyl acetate and n-hexane to give 8-hydroxy-2-methyl-3-(2-propynyl)imidazo[1,2-a]pyridine (1.93 g).

後処理

  1. customevaporated in vacuo
  2. additionTo the residue was added 20% sulfuric acid (75 ml)
  3. extractionextracted with chloroform
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel (30 g) with chloroform
  8. additiona mixture of chloroform and methanol (30:1 to 20:1) as eluents
  9. customThe eluates were evaporated in vacuo
  10. customthe residue was recrystallized from a mixture of ethyl acetate and n-hexane

出典と根拠

ORDレコード
ord-af26c79837a94339b54a759b2a0c90a3
出典データセット
uspto-grants-1988_11
特許番号
US04782055

反応ノート

読み込み中…