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

HRID 1253540ノート

反応式

HRID 1253540 の反応式
[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

参加物

6

反応物 3

HCID 7498Benzyl Bromide2 回HCID 24758Sodium hydrideHCID 67207447HCID 67207447、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-6aa0af6f8a1e4b208e75f245fa0208e7
出典データセット
uspto-grants-2013_06
特許番号
US08455477B2

反応ノート

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