Water → 5-nitro-1-(pyridin-2-ylmethyl)-1H-indazole

HRID 38547

反応式

HRID 38547 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[CH:7]2)([O-:3])=[O:2].Cl.Cl[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1.C(=O)([O-])[O-].[K+].[K+].O>C1COCC1>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)[N:8]=[CH:7]2)([O-:3])=[O:2]

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 215015-NitroindazoleHCID 23392Picolyl chloride hydrochloride

生成物 1

HCID 224961495-nitro-1-(pyridin-2-ylmethyl)-1H-indazole収率 50.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

5-Nitroindazole (10.0 g, 61.3 mmol) was dissolved in THF (100 mL), and 2-(chloromethyl)pyridine hydrochloride (8.60 g, 52.4 mmol) and potassium carbonate (24.4 g, 184 mmol) were added. The mixture was heated for 4 h to 75° C. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and the solvent was removed in vacuo. The crude product was purified by column chromatography on silica gel (eluent: gradient cyclohexane/ethyl acetate 1:1 to ethyl acetate) to yield 6.73 g (43%) of the title compound.

後処理

  1. temperatureThe mixture was heated for 4 h to 75° C
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customthe solvent was removed in vacuo
  5. customThe crude product was purified by column chromatography on silica gel (eluent: gradient cyclohexane/ethyl acetate 1:1 to ethyl acetate)

出典と根拠

ORDレコード
ord-91d9d9e2622743368ade6bd13677bb0a
出典データセット
uspto-grants-2013_09
特許番号
US08524722B2

関連ノート

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