Methyl iodide → 5-Bromo-1-methyl-1H-indazole

HRID 241083

反応式

HRID 241083 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2.[C:11](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[N:6]=[CH:5]2

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 7619295-bromo-1H-indazole

生成物 1

HCID 225587255-Bromo-1-methyl-1H-indazole収率 70%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A suspension of 5-bromo-1H-indazole (200 mg, 1.02 mmol), cesium carbonate (661 mg, 2.00 mmol), and iodomethane (156 mg, 1.10 mmol) in dimethylformamide (3 mL) was stirred at room temperature for 15 h. The mixture was partitioned between 5% lithium chloride and ethyl acetate, the aqueous layer was extracted with ethyl acetate (2×), the combined organic extracts were washed with 1 N sodium hydroxide, and brine, dried over anhydrous sodium sulfate, filtered and concentrated. Column chromatography on silica (hexanes/ethyl acetate 4:1) gave 5-bromo-1-methyl-1H-indazole (150 mg, 70% yield) as an orange solid. MS (EI) for C8H7BrN2: 212 (MH+).

後処理

  1. customThe mixture was partitioned between 5% lithium chloride and ethyl acetate
  2. extractionthe aqueous layer was extracted with ethyl acetate (2×)
  3. washthe combined organic extracts were washed with 1 N sodium hydroxide, and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-16eb5aa2b9ae4a53ac49ff40dc23ac45
出典データセット
uspto-grants-2014_02
特許番号
US08648066B2

関連ノート

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