3,4-dihydro-2H-pyran → 4-bromo-6-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

HRID 475130노트

반응식

HRID 475130 반응식
[Br:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.[CH2:12]1[CH2:17][O:16][CH:15]=[CH:14][CH2:13]1.CC1C=CC(S(O)(=O)=O)=CC=1.O>C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH:15]1[CH2:14][CH2:13][CH2:12][CH2:17][O:16]1

참가 물질

5

반응물 3

HCID 80803,4-dihydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 247288014-Bromo-6-methyl-1H-indazole

생성물 1

HCID 712727704-bromo-6-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole수율 90%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 4-bromo-6-methyl-1H-indazole (1.05 g, 5 mmol), DHP (2.1 g, 25 mmol), and TsOH.H2O (96 mg, 0.5 mmol) in THF (50 ml) under nitrogen was heated at reflux overnight. The reaction mixture was concentrated in vacuo and to the residue was added DCM (300 mL) and water (50 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography by using petroleum ether:EtOAc (100:1) as eluting solvents to afford 4-bromo-6-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole as light yellow oil (1.1 g, 90%) MS (ESI): m/z=295.1 [M+1]+.

후처리

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. concentrationThe reaction mixture was concentrated in vacuo and to the residue
  4. additionwas added DCM (300 mL) and water (50 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel chromatography
  9. washas eluting solvents

출처 및 근거

ORD 기록
ord-db63ac98724044c9ba9a957f45647367
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637537B2

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