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

HRID 1880389노트

반응식

HRID 1880389 반응식
[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

참가 물질

6

반응물 3

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

생성물 2

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-7f05cfa9830944b8a963202eacfa62bf
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318762B2

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