t-Butyl bromide → 2-Isopropyl-3-(1-hydroxy-2,2-dimethylpropyl)pyrazolo[1,5-a]pyridine

HRID 483086노트

반응식

HRID 483086 반응식
[Mg].[C:2](Br)([CH3:5])([CH3:4])[CH3:3].[CH:7]([C:10]1[C:18]([CH:19]=[O:20])=[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][N:12]2[N:11]=1)([CH3:9])[CH3:8].[Cl-].[NH4+]>CCOCC.C1C=CC=CC=1>[CH:7]([C:10]1[C:18]([CH:19]([OH:20])[C:2]([CH3:5])([CH3:4])[CH3:3])=[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][N:12]2[N:11]=1)([CH3:9])[CH3:8]

참가 물질

7

반응물 4

HCID 10485t-Butyl bromideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 143032672-Isopropylpyrazolo[1,5-a]pyridine-3-carbaldehyde

생성물 1

HCID 133917102-Isopropyl-3-(1-hydroxy-2,2-dimethylpropyl)pyrazolo[1,5-a]pyridine수율 52%

시약·촉매·용매 2

HCID 241Benzene용매HCID 3283Diethyl Ether용매2회

실험 절차

To a suspension of 1.6 g of magnesium in 10 ml of dry ether was added a solution of 9.3 g of tert. butylbromide in 15 ml of dry ether under stirring. After the addition was completed, the stirring was continued for an hour at room temperature. To the Grignard reagent were added 2.5 g of 2-isopropyl-3-formylpyrazolo[1,5-a]pyridine in 5 ml of dry benzene under stirring. The mixture was stirred for an hour at room temperature and 11 hours at reflux temperature. The reaction mixture was treated with 100 ml of aqueous 20% ammonium chloride solution and extracted with ether. The ether layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was subjected to silica gel column chromatography, eluted with dichloromethane, to give 1.7 g (52%) of pale yellow crystals, mp 95° C.

후처리

  1. additionAfter the addition
  2. waitthe stirring was continued for an hour at room temperature
  3. stirringunder stirring
  4. stirringThe mixture was stirred for an hour at room temperature and 11 hours
  5. temperatureat reflux temperature
  6. extractionextracted with ether
  7. washThe ether layer was washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo
  10. washeluted with dichloromethane

출처 및 근거

ORD 기록
ord-161c696e45d14edca61a910d1821d2e3
출처 데이터셋
uspto-grants-1986_03
특허 번호
US04578392

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