1-Bromo-2-methylpropane → 1-Isobutyl-5-methoxy-1H-indazole

HRID 909225

반응식

HRID 909225 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][N:7]=[CH:6]2.C([O-])([O-])=O.[K+].[K+].Br[CH2:19][CH:20]([CH3:22])[CH3:21]>CN(C=O)C>[CH2:19]([N:8]1[C:9]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=2)[CH:6]=[N:7]1)[CH:20]([CH3:22])[CH3:21]

참가 물질

5

반응물 3

HCID 65551-Bromo-2-methylpropane2회HCID 11430Potassium CarbonateHCID 133468605-Methoxy-1H-indazole

생성물 1

HCID 574187691-Isobutyl-5-methoxy-1H-indazole수율 36.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 5-methoxy-1H-indazole (5.00 g, 33.7 mmol) in DMF (100 mL) was treated with K2CO3 (5.83 g, 42.2 mmol) and stirred at room temperature for 15 minutes. To this solution was added 1-bromo-2-methylpropane (5.09 g, 37.1 mmol) and the resulting mixture was heated to 110° C. for 18 hours. Another equivalent of 1-bromo-2-methyl-propane was added and the mixture continued to heat for 48 hours more. The mixture was concentrated under reduced pressure and dissolved in dichloromethane. The solution was washed with 1N HCl, filtered, and concentrated under reduced pressure. The residue was chromatographed on Biotage eluting with hexanes/ether (5:1) to afford 2.51 g of orange oil (36% yield).

후처리

  1. temperaturethe resulting mixture was heated to 110° C. for 18 hours
  2. temperatureto heat for 48 hours more
  3. concentrationThe mixture was concentrated under reduced pressure
  4. dissolutiondissolved in dichloromethane
  5. washThe solution was washed with 1N HCl
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was chromatographed on Biotage
  9. washeluting with hexanes/ether (5:1)

출처 및 근거

ORD 기록
ord-f454034d95eb45a5b94538c28779b71f
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017641B2

연결된 노트

불러오는 중…