Lithium Hydroxide → 8-((2,6-Difluorobenzyl)oxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid

HRID 1624060ノート

反応式

HRID 1624060 の反応式
[F:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([C:16]([O:18]CC)=[O:17])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1.[OH-].[Li+]>C1COCC1.CO>[F:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([C:16]([OH:18])=[O:17])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 86717871Ethyl 8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylate

生成物 1

HCID 867178728-((2,6-Difluorobenzyl)oxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid

試薬・触媒・溶媒 1

HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

107 g of ethyl 8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylate (Example 5A; 300 mmol, 1 equivalent) were dissolved in 2.8 l of THF/methanol (1:1), 1.5 l of 1 N aqueous lithium hydroxide solution (1.5 mol, 5 equivalents) were added and the mixture was stirred at RT for 16 h. The organic solvents were removed under reduced pressure and the resulting aqueous solution was adjusted in an ice bath to pH 3-4 using 1 N aqueous hydrochloric acid. The resulting solid was filtered off, washed with water and isopropanol and dried under reduced pressure. This gave 92 g (95% of theory) of the title compound.

後処理

  1. customThe organic solvents were removed under reduced pressure
  2. customthe resulting aqueous solution was adjusted in an ice bath to pH 3-4
  3. filtrationThe resulting solid was filtered off
  4. washwashed with water and isopropanol
  5. customdried under reduced pressure

出典と根拠

ORDレコード
ord-bc4f365b5772495293511c56274432f7
出典データセット
uspto-grants-2014_07
特許番号
US08778964B2

反応ノート

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