4-Heptanone → 4-(7-bromo-2-methyl-2H-indazol-3-yl)-heptan-4-ol

HRID 902553ノート

反応式

HRID 902553 の反応式
[Br:1][C:2]1[C:10]2[C:6](=[CH:7][N:8]([CH3:11])[N:9]=2)[CH:5]=[CH:4][CH:3]=1.C([N-]C(C)C)(C)C.[Li+].CCCCCCC.C(C1C=CC=CC=1)C.C1COCC1.[CH3:40][CH2:41][CH2:42][C:43](=[O:47])[CH2:44][CH2:45][CH3:46].C([O-])(O)=O.[Na+]>C1COCC1>[Br:1][C:2]1[C:10]2[C:6](=[C:7]([C:43]([OH:47])([CH2:44][CH2:45][CH3:46])[CH2:42][CH2:41][CH3:40])[N:8]([CH3:11])[N:9]=2)[CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 5

HCID 312464-HeptanoneHCID 516892Sodium BicarbonateHCID 2724682Lithium diisopropylamideHCID 210945807-bromo-2-methyl-2H-indazoleHCID 22742125Tetrahydrofuran heptane ethylbenzol

生成物 1

HCID 210945894-(7-bromo-2-methyl-2H-indazol-3-yl)-heptan-4-ol収率 78%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
2.5 °C

実験手順

To a solution of 7-bromo-2-methyl-2H-indazole (1.5 g, 7.1 mmol) in 18 mL of THF at −78° C. was added a 2 M solution of lithium diisopropylamide in heptane/ethylbenzene/THF (5.3 mL, 11 mmol). The solution was stirred at 0-5° C. for 10 m, then rechilled to −78° C. To it was added 4-heptanone (1.49 mL, 10.6 mmol), and the solution was stirred overnight, allowing to slowly warm to room temperature. A saturated aqueous NaHCO3 solution (40 mL) was added, and the mixture was extracted with three 30 mL portions of ethyl acetate. The combined organic layers were dried over Na2SO4, filtered, and concentrated to a brown solid. Column chromatography (0→20% EtOAc/hexanes) afforded 4-(7-bromo-2-methyl-2H-indazol-3-yl)-heptan-4-ol (42; 1.80 g; 78%).

後処理

  1. customrechilled to −78° C
  2. stirringthe solution was stirred overnight
  3. temperatureto slowly warm to room temperature
  4. extractionthe mixture was extracted with three 30 mL portions of ethyl acetate
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to a brown solid

出典と根拠

ORDレコード
ord-ef09b8f2e6f547d09b8fcedd28f5bf1f
出典データセット
uspto-grants-2008_04
特許番号
US07365211B2

反応ノート

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