p-Toluenesulfonic acid → 4-Bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

HRID 1047285Notes

Reaction equation

HRID 1047285 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.[O:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCCC1>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][O:11]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 223525484-bromo-1H-indazole

Product 1

HCID 574747294-Bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazoleYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-bromo-1H-indazole (1.82 g, 9.24 mmol), 3,4-dihydro-2H-pyran (1.55 g, 18.48 mmol) and toluene-4-sulfonic acid (0.26 g, 1.39 mmol) in anhydrous tetrahydrofuran (40 mL) was heated at 80° C. overnight under nitrogen. The solvent was removed under reduced pressure and the residue was purified on silica gel column (3% ethyl acetate in petroleum ether) to give the title compound (2.13 g, 81% yield) as a yellow solid. MS (ESI): m/z 280.9 [M+1]+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified on silica gel column (3% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-be3c2c15617d4805bc2d1311b23e8ed7
Source dataset
uspto-grants-2013_10
Patent number
US08569494B2

Reaction notes

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