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

HRID 2357906
ノート
印刷プレビュー

反応式

HRID 2357906 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-40 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-30203758a01747ada5ae61e99c008368
出典データセット
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07763617B2

反応ノート

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