Isopropyl iodide → Ethyl 5-fluoro-1-isopropyl-1H-indazole-3-carboxylate

HRID 602479노트

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HRID 602479 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[C:11]([O:13][CH2:14][CH3:15])=[O:12].[CH3:16][C:17](C)([O-])[CH3:18].[K+].IC(C)C>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:17]([CH3:18])[CH3:16])[N:6]=[C:5]2[C:11]([O:13][CH2:14][CH3:15])=[O:12]

참가 물질

5

반응물 3

HCID 6362Isopropyl iodideHCID 12689362Ethyl 5-fluoro-1H-indazole-3-carboxylateHCID 23665647Potassium tert-butoxide

생성물 1

HCID 67271032Ethyl 5-fluoro-1-isopropyl-1H-indazole-3-carboxylate수율 35.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a stirred solution of ethyl 5-fluoro-1H-indazole-3-carboxylate (487 mg, 2.3 mmol, J. Heterocycl. Chem. 1964, 1, 239-241) in tetrahydrofuran (4 mL) was added potassium tert-butoxide (289 mg, 2.57 mmol) at 0° C. After stirring at 0° C. for 1 h, 2-iodopropane (438 mg, 2.57 mmol) was added to the mixture. The resulting mixture was stirred at room temperature for 20 h and concentrated under reduced pressure. The mixture was diluted with ethyl acetate (50 mL), washed with water (30 mL) and brine (30 mL). The organic layer was separated, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (10:1 to 2:1) to give 205 mg (35%) of the title compound as a yellow crystal.

후처리

  1. stirringThe resulting mixture was stirred at room temperature for 20 h
  2. concentrationconcentrated under reduced pressure
  3. additionThe mixture was diluted with ethyl acetate (50 mL)
  4. washwashed with water (30 mL) and brine (30 mL)
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (10:1 to 2:1)

출처 및 근거

ORD 기록
ord-5de1ff1ecfd14f49a76de2612b6b71c6
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906532B2

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