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Ammonium Chloride → 2-Trifluoromethyl-4-(1-hydroxyethyl)-7-methoxy-pyrazolo[1,5-a]pyridine

HRID 2357906
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HRID 2357906 반응식
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:15]=[C:6]2[C:7]([CH:13]=[O:14])=[CH:8][CH:9]=[C:10]([O:11][CH3:12])[N:5]2[N:4]=1.[CH3:18][Mg]Br.C1COCC1.[Cl-].[NH4+]>C1COCC1>[F:17][C:2]([F:1])([F:16])[C:3]1[CH:15]=[C:6]2[C:7]([CH:13]([OH:14])[CH3:18])=[CH:8][CH:9]=[C:10]([O:11][CH3:12])[N:5]2[N:4]=1
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참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 593893517-Methoxy-2-(trifluoromethyl)pyrazolo[1,5-a]pyridine-4-carbaldehydeHCID 178420675HCID 178420675, 화합물

생성물 1

HCID 593893232-Trifluoromethyl-4-(1-hydroxyethyl)-7-methoxy-pyrazolo[1,5-a]pyridine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-40 °C

실험 절차

The compound of Example 115 (1.63 g) was dissolved in THF (70.0 mL) in an argon atmosphere. While the solution was kept at −78° C., 0.90 mol/L methyl magnesium bromide/THF solution (8.90 mL) was added dropwise and the mixture was stirred for 1.5 hours as it was allowed to gradually warm to −40° C. Subsequently, a saturated aqueous solution of ammonium chloride was added and the mixture was extracted with ethyl acetate. 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=1:1) afforded the title compound as a white powder (1.64 g).

후처리

  1. customwas kept at −78° C.
  2. extractionthe mixture was extracted with ethyl acetate
  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=1:1)

출처 및 근거

ORD 기록
ord-30203758a01747ada5ae61e99c008368
출처 데이터셋
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07763617B2

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