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

HRID 602479ノート

反応式

HRID 602479 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-5de1ff1ecfd14f49a76de2612b6b71c6
出典データセット
uspto-grants-2011_03
特許番号
US07906532B2

反応ノート

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