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

HRID 909225

反応式

HRID 909225 の反応式
[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]

参加物

5

反応物 3

HCID 65551-Bromo-2-methylpropane2 回HCID 11430Potassium CarbonateHCID 133468605-Methoxy-1H-indazole

生成物 1

HCID 574187691-Isobutyl-5-methoxy-1H-indazole収率 36.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-f454034d95eb45a5b94538c28779b71f
出典データセット
uspto-grants-2011_09
特許番号
US08017641B2

関連ノート

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