Methyl iodide → Methyl 1-methyl-1H-indazole-6-carboxylate

HRID 878555

반응식

HRID 878555 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=2)[CH:3]=[N:2]1.[H-].[Na+].[CH3:16]I>O>[CH3:16][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=2)[CH:3]=[N:2]1.[CH3:16][N:2]1[CH:3]=[C:4]2[C:9]([CH:8]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[CH:6]=[CH:5]2)=[N:1]1

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 286535methyl 1H-indazole-6-carboxylate

생성물 2

HCID 22598983Methyl 1-methyl-1H-indazole-6-carboxylateHCID 37818688Methyl 2-methyl-2H-indazole-6-carboxylate

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To an ice-cooled solution of methyl 1H-indazole-6-carboxylate (566 mg, 3.21 mmol) was added NaH (154 mg, 3.85 mmol), the mixture was then stirred at room temperature for 30 min. Methyl iodide (547 mg, 3.85 mmol) was added drop wise, and the reaction mixture was stirred overnight. Cooled to 0° C., added water and extracted with ethyl acetate. The organic phase was concentrated and purified by gel chromatograph to provide 130 mg of methyl 1-methyl-1H-indazole-6-carboxylate and 230 mg of methyl 2-methyl-2H-indazole-6-carboxylate, 59%. 1H NMR for methyl 1-methyl-1H-indazole-6-carboxylate: 1H NMR (400 MHz, CDCl3): δ 3.97 (3H, s), 4.14 (3H, s), 7.74-7.82 (2H, m), 8.02 (1H, s), 8.17 (1H, d, J=0.8 Hz). 1H NMR for methyl 2-methyl-2H-indazole-6-carboxylate: 1H NMR (400 MHz, CDCl3): δ 3.94 (3H, s), 4.25 (3H, s), 7.65-7.72 (2H, m), 7.92 (1H, s), 8.47 (1H, d, J=1.2 Hz). [M+H] Calc'd for C10H10N2O2, 191; Found, 191.

후처리

  1. stirringthe reaction mixture was stirred overnight
  2. temperatureCooled to 0° C.
  3. extractionextracted with ethyl acetate
  4. concentrationThe organic phase was concentrated
  5. custompurified by gel chromatograph

출처 및 근거

ORD 기록
ord-30ead9d02bdd46d18074fdc6215cebc2
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987461B2

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