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

HRID 902553

반응식

HRID 902553 반응식
[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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
2.5 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-ef09b8f2e6f547d09b8fcedd28f5bf1f
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07365211B2

연결된 노트

불러오는 중…