ethyl 4-azido-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate → Ethyl 4-amino-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

HRID 497959ノート

反応式

HRID 497959 の反応式
[N:1]([C:4]1[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][N:7]=[C:6]2[N:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[N:16]=[C:17]([CH3:18])[C:5]=12)=[N+]=[N-]>C(O)C.[C].[Pd]>[NH2:1][C:4]1[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][N:7]=[C:6]2[N:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[N:16]=[C:17]([CH3:18])[C:5]=12

参加物

4

反応物 1

HCID 22320288ethyl 4-azido-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

生成物 1

HCID 22320361Ethyl 4-amino-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate収率 96%

試薬・触媒・溶媒 2

HCID 178418390HCID 178418390、化合物触媒HCID 702Ethanol溶媒

実験手順

A solution of ethyl 4-chloro-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (1.0 g, 3.2 mmol) and sodium azide (0.23 g, 3.5 mmol) in N,N-dimethylformamide (5 mL) was heated and stirred at 100° C. for 30 minutes. The solution was cooled to room temperature, and poured into water, and the resulting solution was made basic by the addition of an aqueous sodium hydroxide solution, and organic matter was extracted with chloroform. The extract was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give ethyl 4-azido-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate. To a solution of the ethyl 4-azido-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate in ethanol (150 mL) was added 10% palladium-carbon (1.2 g, 50% hydrate), and the mixture was stirred at room temperature for 1 hour under hydrogen atmosphere. The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure. Purification of the residue by silica gel column chromatography (basic silica gel, ethyl acetate:methanol=93:7) gave the title compound (900 mg, 96% yield).

後処理

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customPurification of the residue by silica gel column chromatography (basic silica gel, ethyl acetate:methanol=93:7)

出典と根拠

ORDレコード
ord-c17e1aacafcd469ca8d04ce1802265df
出典データセット
uspto-grants-2005_09
特許番号
US06949648B2

反応ノート

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