Phosphorus oxybromide → 3-bromo-7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridine

HRID 916208ノート

反応式

HRID 916208 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[N:10]1[CH2:15][CH2:14][CH2:13][C:12]2[C:16](=O)[N:17]([CH3:19])[NH:18][C:11]1=2.P(Br)(Br)([Br:23])=O>ClCCl>[Br:23][C:16]1[N:17]([CH3:19])[N:18]=[C:11]2[C:12]=1[CH2:13][CH2:14][CH2:15][N:10]2[C:3]1[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[Cl:1]

参加物

4

反応物 2

HCID 24613Phosphorus oxybromideHCID 12143941HCID 12143941、化合物

生成物 1

HCID 113602163-bromo-7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridine収率 30.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
110 °C

実験手順

7-(2-Chloro-4,6-dimethylphenyl)-2-methyl-1,2,4,5,6,7-hexahydropyrazolo[3,4-b]pyridin-3-one (3.16 g) and phosphorus oxybromide (15.5 g) were combined and stirred in a 110° C. oil bath for 4 h. After the reaction mixture had cooled to room temperature, it was dissolved in dichloromethane and added to 200 mL of ice/water. This mixture was stirred vigorously for 30 min. The phases were then separated and the aqueous phase was washed with additional dichloromethane. The combined organic phases were washed with aqueous sodium bicarbonate, dried with magnesium sulfate, and concentrated on the rotary evaporator. The residue was chromatographed on silica gel eluting with an acetone/hexane gradient to provide 1.16 g of 3-bromo-7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridine, mp 106-107° C.

後処理

  1. temperatureAfter the reaction mixture had cooled to room temperature
  2. stirringThis mixture was stirred vigorously for 30 min
  3. customThe phases were then separated
  4. washthe aqueous phase was washed with additional dichloromethane
  5. washThe combined organic phases were washed with aqueous sodium bicarbonate
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated on the rotary evaporator
  8. customThe residue was chromatographed on silica gel eluting with an acetone/hexane gradient

出典と根拠

ORDレコード
ord-9fabad48be1c40cf830ef78faf92a189
出典データセット
uspto-grants-2007_09
特許番号
US07268146B2

反応ノート

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