Methyl iodide → 5-Bromo-4-methoxy-1-methyl-1H-indazole

HRID 1056982ノート

反応式

HRID 1056982 の反応式
[Br:1][C:2]1[C:3]([O:11][CH3:12])=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2.[H-].[Na+].[CH3:15]I>CN(C)C=O.O.C(OCC)(=O)C>[Br:1][C:2]1[C:3]([O:11][CH3:12])=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:15])[N:6]=[CH:5]2

参加物

7

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 231345645-bromo-4-methoxy-1H-indazole

生成物 1

HCID 847023345-Bromo-4-methoxy-1-methyl-1H-indazole収率 66%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
20 °C

実験手順

A solution of 5-bromo-4-methoxy-1H-indazole (0.125 g, 0.550 mmol) in N,N-dimethylformamide (2.20 mL) was treated with sodium hydride (0.0166 g, 0.659 mmol) at 20° C. and then stirred at 20° C. for 30 min. The resultant reaction mixture was treated with methyl iodide (0.0410 mL, 0.658 mmol) and stirred at 20° C. for 1 h. The reaction mixture was diluted with water and ethyl acetate. Layers were separated and the organic layer was washed with brine, dried with sodium sulfate, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (100% hexanes to 100% EtOAc) gave the desired product (87 mg, 66%) as a white solid. LCMS calculated for C9H10BrN2O (M+H)+: m/z=241.0, 243.0. found: 240.9, 242.9.

後処理

  1. customThe resultant reaction mixture
  2. stirringstirred at 20° C. for 1 h
  3. customLayers were separated
  4. washthe organic layer was washed with brine
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give the crude product
  9. customPurification by flash column chromatography (100% hexanes to 100% EtOAc)

出典と根拠

ORDレコード
ord-4053e82448a041d39a3fc4895374e4b1
出典データセット
uspto-grants-2016_07
特許番号
US09399640B2

反応ノート

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