Water → 4-Hydroxymethyl-7-iodo-2-trifluoromethylpyrazolo[1,5-a]pyridin

HRID 2357900ノート

反応式

HRID 2357900 の反応式
[Si]([O:8][CH2:9][C:10]1[C:11]2[N:12]([N:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:19]=2)[C:13]([I:16])=[CH:14][CH:15]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.O>O1CCCC1>[F:23][C:20]([F:21])([F:22])[C:18]1[CH:19]=[C:11]2[C:10]([CH2:9][OH:8])=[CH:15][CH:14]=[C:13]([I:16])[N:12]2[N:17]=1

参加物

5

反応物 3

HCID 962WaterHCID 11078149TBAF tetrahydrofuranHCID 580140154-(t-Butyldimethylsilyloxymethyl)-7-iodo-2-trifluoromethylpyrazolo[1,5-a]pyridine

生成物 1

HCID 593893564-Hydroxymethyl-7-iodo-2-trifluoromethylpyrazolo[1,5-a]pyridin収率 95.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

The compound of Example 92 (4.57 g) was dissolved in tetrahydrofuran (50.0 mL). While this solution was chilled in an ice bath, 1.0 mol/L tetran-butyl ammonium fluoride/tetrahydrofuran solution (12.0 mL) was added and the mixture was stirred at room temperature for 1 hour. Subsequently, water was added and the reaction mixture was extracted with ethylacetate. The organic layer was washed sequentially with water and saturated brine and dried over anhydrous sodium sulfate. Evaporation of the solvent and subsequent purification of the residue by silica gel column chromatography (hexane:ethyl acetate=2:1) afforded the title compound as a pale yellow powder (3.26 g).

後処理

  1. temperatureWhile this solution was chilled in an ice bath
  2. extractionthe reaction mixture was extracted with ethylacetate
  3. washThe organic layer was washed sequentially with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customEvaporation of the solvent and subsequent purification of the residue by silica gel column chromatography (hexane:ethyl acetate=2:1)

出典と根拠

ORDレコード
ord-2182e7a5147f4fbda759c941b72298b4
出典データセット
uspto-grants-2010_07
特許番号
US07763617B2

反応ノート

読み込み中…