Benzyl Bromide → 4-(Benzyloxy)-6-bromopyrazolo[1,5-a]pyridine

HRID 1253540노트

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HRID 1253540 반응식
[Br:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5]2[N:6]([N:8]=[CH:9][CH:10]=2)[CH:7]=1.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[H-].[Na+]>CN(C=O)C.C(OCC)C>[CH2:12]([O:11][C:4]1[C:5]2[N:6]([N:8]=[CH:9][CH:10]=2)[CH:7]=[C:2]([Br:1])[CH:3]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

6

반응물 3

HCID 7498Benzyl Bromide2회HCID 24758Sodium hydrideHCID 67207447HCID 67207447, 화합물

생성물 1

HCID 673757094-(Benzyloxy)-6-bromopyrazolo[1,5-a]pyridine

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

6-bromopyrazolo[1,5-a]pyridin-4-ol (1.10 g, 5.16 mmol) and benzyl bromide (0.676 ml, 5.68 mmol) were dissolved in DMF (20 ml) at 0° C. NaH (413 mg, 10.3 mmol, 60 wt %) was added in one portion and the mixture was allowed to stir at 0° C. After 30 minutes, additional benzyl bromide 0.068 ml, 0.57 mmol) was added and the mixture was allowed to stir 30 minutes at 0° C. The reaction mixture was diluted in diethyl ether, washed with saturated aqueous sodium hydrogen carbonate and brine then dried over magnesium sulfate, filtered and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate/isohexane gradient) to afford 4-(benzyloxy)-6-bromopyrazolo[1,5-a]pyridine.

후처리

  1. stirringto stir 30 minutes at 0° C
  2. washwashed with saturated aqueous sodium hydrogen carbonate and brine
  3. dry with materialthen dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (ethyl acetate/isohexane gradient)

출처 및 근거

ORD 기록
ord-6aa0af6f8a1e4b208e75f245fa0208e7
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455477B2

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