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

HRID 916208노트

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HRID 916208 반응식
[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]

참가 물질

4

반응물 2

HCID 24613Phosphorus oxybromideHCID 12143941HCID 12143941, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
110 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9fabad48be1c40cf830ef78faf92a189
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07268146B2

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