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

HRID 1880389ノート

反応式

HRID 1880389 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[C:14]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C>[CH3:14][N:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[CH3:14][N:2]1[CH:3]=[C:4]2[C:9]([CH:8]=[CH:7][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:5]2)=[N:1]1

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 22260640Methyl 1H-indazole-5-carboxylate

生成物 2

HCID 37818676Methyl 1-methyl-1H-indazole-5-carboxylate収率 40%HCID 37818686Methyl 2-methyl-2H-indazole-5-carboxylate収率 8.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of methyl 1H-indazole-5-carboxylate (2.5 g, 14 mmol) in DMF (45 mL) was added K2CO3 (4.90 g, 35.5 mmol) followed by iodomethane (1.77 mL, 28.4 mmol). The mixture was stirred at room temperature for 2 hours and then heated at 50° C. overnight. The mixture was concentrated, dissolved in EtOAc and washed with saturated aqueous NaCl. The organic extract was dried over Na2SO4, filtered and concentrated. The crude material was purified by CombiFlash (80 g column, 25-45% EtOAc/heptane) to provide methyl 1-methyl-1H-indazole-5-carboxylate (1.07 g, 40%) and methyl 2-methyl-2H-indazole-5-carboxylate (227 mg, 8.4%).

後処理

  1. temperatureheated at 50° C. overnight
  2. concentrationThe mixture was concentrated
  3. dissolutiondissolved in EtOAc
  4. washwashed with saturated aqueous NaCl
  5. extractionThe organic extract
  6. dry with materialwas dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude material was purified by CombiFlash (80 g column, 25-45% EtOAc/heptane)

出典と根拠

ORDレコード
ord-7f05cfa9830944b8a963202eacfa62bf
出典データセット
uspto-grants-2012_11
特許番号
US08318762B2

反応ノート

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