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

HRID 2357900노트

반응식

HRID 2357900 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-2182e7a5147f4fbda759c941b72298b4
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07763617B2

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