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

HRID 2357908ノート

反応式

HRID 2357908 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.[CH2:18]([Mg]Br)[CH2:19][CH3:20].O1CCCC1.[Cl-].[NH4+]>O1CCCC1>[OH:14][CH:13]([C:7]1[C:6]2[N:5]([N:4]=[C:3]([C:2]([F:1])([F:16])[F:17])[CH:15]=2)[C:10]([O:11][CH3:12])=[CH:9][CH:8]=1)[CH2:18][CH2:19][CH3:20]

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 593893517-Methoxy-2-(trifluoromethyl)pyrazolo[1,5-a]pyridine-4-carbaldehydeHCID 178420656HCID 178420656、化合物

生成物 1

HCID 593892794-(1-Hydroxybutyl)-7-methoxy-2-trifluoromethyl-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 (300 mg) was dissolved in tetrahydrofuran (12.0 mL) in an argon atmosphere. While this solution was kept at −78° C., 1.04 mol/L n-propyl magnesium bromide/tetrahydrofuran solution (1.40 mL) was added dropwise and the mixture was stirred for 3 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 yellow oil (265 mg).

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-562e649230ef44d48b6ab6e2f3cb7473
出典データセット
uspto-grants-2010_07
特許番号
US07763617B2

反応ノート

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