Sodium hydride → 1-benzyloxymethyl-4-chloro-1H-pyrazolo[3,4-b]pyridine

HRID 2070018ノート

反応式

HRID 2070018 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[CH:10][C:3]=12.[H-].[Na+].[CH2:13]([O:20][CH2:21]Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C>[CH2:13]([O:20][CH2:21][N:8]1[C:4]2=[N:5][CH:6]=[CH:7][C:2]([Cl:1])=[C:3]2[CH:10]=[N:9]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 137983Benzyl chloromethyl etherHCID 3100454-Chloro-1H-pyrazolo[3,4-b]pyridine

生成物 1

HCID 593985441-benzyloxymethyl-4-chloro-1H-pyrazolo[3,4-b]pyridine収率 58.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

4-Chloro-1H-pyrazolo[3,4-b]pyridine (371 mg, 2.42 mmol) was dissolved in anhydrous DMF (1 mL), and sodium hydride (60%, 116 mg, 2.42 mmol) was added thereto. The resulting mixture was stirred under ice-cooling for 30 minutes, and then benzyloxymethyl chloride (0.48 mL, 3.39 mmol) was added thereto. The resulting mixture was stirred under ice-cooling for 1 hour and concentrated under reduced pressure. The residue was partitioned between ethyl acetate (80 mL) and saturated brine (20 mL). The aqueous layer was further extracted with ethyl acetate (70 mL). The combined organic layer was washed with saturated brine, dried, and concentrated. The residue was purified by silica-gel column chromatography (Fuji Silysia, BW300, 70 g, n-hexane:EtOAc=5:1) to give 1-benzyloxymethyl-4-chloro-1H-pyrazolo[3,4-b]pyridine as a light-yellow syrup (386 mg, yield: 58%).

後処理

  1. temperaturecooling for 30 minutes
  2. stirringThe resulting mixture was stirred under ice-
  3. temperaturecooling for 1 hour
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was partitioned between ethyl acetate (80 mL) and saturated brine (20 mL)
  6. extractionThe aqueous layer was further extracted with ethyl acetate (70 mL)
  7. washThe combined organic layer was washed with saturated brine
  8. customdried
  9. concentrationconcentrated
  10. customThe residue was purified by silica-gel column chromatography (Fuji Silysia, BW300, 70 g, n-hexane:EtOAc=5:1)

出典と根拠

ORDレコード
ord-f274fe4a7493471883e4e9e99d91dac9
出典データセット
uspto-grants-2012_10
特許番号
US08299252B2

反応ノート

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