Methyl iodide → 3-Iodo-1-methyl-1H-pyrazolo[3,4-B]pyridine

HRID 246565

反応式

HRID 246565 の反応式
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:4][N:3]=1.[CH3:11]C(C)([O-])C.[K+].IC>C1COCC1.O>[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH3:11])[N:3]=1

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 178506575HCID 178506575、化合物

生成物 1

HCID 534706403-Iodo-1-methyl-1H-pyrazolo[3,4-B]pyridine収率 31%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of 3-iodo-1H-pyrazolo[3,4-b]pyridine (3.5 g, 14.3 mmol) in THF (70 mL) at 0° C. was added potassium tert-butoxide (1.92 g, 17.1 mmol) and the reaction mixture stirred at 0° C. for 1 h. Iodomethane (2.43 g, 1.07 mL, 17.1 mmol) was added drop-wise, then the mixture was warmed to rt. After 6 h the mixture was diluted with water, extracted with dichloromethane, then the combined organic phases were dried (MgSO4), filtered and concentrated in vacuo. Purification by chromatography (silica, 20-60% ethyl acetate in hexanes) gave 3-iodo-1-methyl-1H-pyrazolo[3,4-b]pyridine (1.14 g, 4.4 mmol, 31%) as an off-white solid. MS (M+H)+=260.

後処理

  1. temperaturethe mixture was warmed to rt
  2. extractionextracted with dichloromethane
  3. dry with materialthe combined organic phases were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by chromatography (silica, 20-60% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-750f9ba1df90465aaebfddd99af7669b
出典データセット
uspto-grants-2014_02
特許番号
US08658646B2

関連ノート

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