3,4-dihydro-2H-pyran → HCID 71272199, compound

HRID 475158Notes

Reaction equation

HRID 475158 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.[O:15]1[CH:20]=[CH:19][CH2:18][CH2:17][CH2:16]1>C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:12])[F:13])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][O:15]1

Participants

4

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 247292324-Bromo-6-(trifluoromethyl)-1H-indazole

Product 1

HCID 71272199HCID 71272199, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A round-bottom flask was charged with 4-bromo-6-(trifluoromethyl)-1H-indazole (1.00 g, 3.8 mmol), TsOH monohydrate (27 mg, 0.15 mmol), 3,4-dihydro-2H-pyran (1.59 g, 18.9 mmol), and THF (25 mL). The reaction mixture was degassed with nitrogen and heated under reflux for 18 h, and then the solvent was removed in vacuo. The residue was purified by SiO2 chromatography to afford 4-bromo-1-(tetrahydro-2H-pyran-2-yl)-6-(trifluoromethyl)-1H-indazole (1.03 g, 78%) as a yellow oil. MS (ESI) m/z: 265.2 [(M−THP group)+1]+.

Workup

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

Sources & evidence

ORD record
ord-1919b119dfc74c4a96ae5e9171c7af40
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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