Methyl iodide → (6-bromo-3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)methanol

HRID 1599295ノート

反応式

HRID 1599295 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([CH2:11][OH:12])[NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].[CH3:15]I>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([CH2:11][OH:12])[N:8]([CH3:15])[C:5]2=[N:6][CH:7]=1

参加物

5

反応物 3

HCID 6328Methyl iodide2 回HCID 24758Sodium hydrideHCID 178519921HCID 178519921、化合物

生成物 1

HCID 10681601(6-bromo-3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)methanol

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A procedure similar to that described in Preparation 15 was repeated, except that the reaction was conducted using 3.00 g of 6-bromo-2-hydroxymethyl-3H-imidazo[5,4-b]pyridine (prepared as described in Preparation 58), 0.58 g of sodium hydride (as a 55% by weight dispersion in mineral oil), 0.92 ml of methyl iodide and 60 ml of dimethylformamide. After completion of the reaction with methyl iodide, the reaction mixture was freed from dimethylformamide by distillation under reduced pressure. The residue was diluted with water, after which it was extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous sodium sulfate, after which the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 50:1 by volume mixture of ethyl acetate and methanol as the eluent, to give 1.40 g of the title compound, melting at 142°-144° C.

後処理

  1. customA procedure similar to that described in Preparation 15
  2. distillationthe reaction mixture was freed from dimethylformamide by distillation under reduced pressure
  3. additionThe residue was diluted with water
  4. extractionafter which it was extracted with ethyl acetate
  5. washThe extract was washed with an aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customafter which the solvent was removed by distillation under reduced pressure
  8. customThe resulting residue was purified by column chromatography through silica gel
  9. additionby volume mixture of ethyl acetate and methanol as the eluent

出典と根拠

ORDレコード
ord-1c7b649418114e2f86d1bdfcd96aab12
出典データセット
uspto-grants-1998_04
特許番号
US05739345

反応ノート

読み込み中…