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

HRID 475161Notes

Reaction equation

HRID 475161 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.[O:13]1[CH:18]=[CH:17][CH2:16][CH2:15][CH2:14]1>C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][O:13]1

Participants

4

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 247283154-Bromo-6-methoxy-1H-indazole

Product 1

HCID 712726524-bromo-6-methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-indazoleYield 111.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A round-bottom flask was charged with 4-bromo-6-methoxy-1H-indazole (1.00 g, 4.40 mmol), TsOH monohydrate (39 mg, 0.22 mmol), 3,4-dihydro-2H-pyran (1.48 g, 17.6 mmol), and THF (40 mL). The reaction mixture was degassed with nitrogen and refluxed for 18 h, and the solvent was then removed in vacuo. The residue was purified by SiO2 chromatography to afford 4-bromo-6-methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (1.53 g, quantitative) as a yellow solid. MS (ESI) m/z: 311.2 [M+1]+.

Workup

  1. customThe reaction mixture was degassed with nitrogen
  2. temperaturerefluxed for 18 h
  3. customthe solvent was then removed in vacuo
  4. customThe residue was purified by SiO2 chromatography

Sources & evidence

ORD record
ord-7cd624c9808944f895df6a8821c90150
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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