Methyl iodide → Methyl 6-bromo-1-methyl-1H-indazole-3-carboxylate

HRID 1689785노트

반응식

HRID 1689785 반응식
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([O:13][CH3:14])=[O:12])=[N:7][NH:8]2)=[CH:4][CH:3]=1.[C:15](=O)([O-])[O-].[K+].[K+].CI>C(#N)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([O:13][CH3:14])=[O:12])=[N:7][N:8]2[CH3:15])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 46784006Methyl 6-bromo-1H-indazole-3-carboxylate

생성물 1

HCID 46942338Methyl 6-bromo-1-methyl-1H-indazole-3-carboxylate수율 70%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a mixture of methyl 6-bromo-1H-indazole-3-carboxylate (0.50 g, 1.96 mmol) and potassium carbonate (1.28 g, 9.29 mmol) in acetonitrile (15 mL) is added methyl iodide (1.31 g, 9.29 mmol) at room temperature. The reaction mixture is stirred at room temperature for 15 h. Remove the solvent under vacuum, dilute with water, and extract with ethyl acetate (3×10 mL). The combined organics are dried over sodium sulfate and concentrated under reduced pressure. The crude is purified by flash chromatography eluting with 8:2 hexane/ethyl acetate to give 0.35 g (70%) of the title compound as an off white solid. 1H NMR (400 MHz, CDCl3) δ 4.03 (s, 3H), 4.14 (s, 3H), 7.42 (dd, J=8.4, 1.2 Hz, 1H), 7.66 (s, 1H), 8.08 (d, J=8.8 Hz, 1H).

후처리

  1. customRemove the solvent under vacuum
  2. additiondilute with water
  3. extractionextract with ethyl acetate (3×10 mL)
  4. dry with materialThe combined organics are dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude is purified by flash chromatography
  7. washeluting with 8:2 hexane/ethyl acetate

출처 및 근거

ORD 기록
ord-b966b5743a9545c29c40b4b9afc75f2f
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153624B2

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