3,4-dihydro-2H-pyran → 5-bromo-1-(oxan-2-yl)-1H-indazole

HRID 1911909Notes

Reaction equation

HRID 1911909 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]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.[NH+]1C=CC=CC=1>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][O:11]1)[N:6]=[CH:5]2

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 7619295-bromo-1H-indazole

Product 1

HCID 534338265-bromo-1-(oxan-2-yl)-1H-indazoleYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 250 mL round bottom flask with was charged with 5-bromo-1H-indazole (25.00 g, 0.127 mol, 1.0 eq), and dichloromethane (100 mL). To the suspension was added dihydropyran (32.0 g, 0.381 mol, 3.0 eq) and a catalytic amount of pyridinium para-toluenesulfonate (3.19 g, 0.0127 mol, 0.10 eq). The mixture was stirred overnight, and in the morning was a clear solution. The methylene chloride was washed sequentially with saturated sodium bicarbonate, 10% citric acid, and brine, and was then evaporated. Chromatography of the residue on silica gel, eluting with EtOAc/heptane, gave the title compound as a colorless liquid (28.00 g, 79%).

Workup

  1. washThe methylene chloride was washed sequentially with saturated sodium bicarbonate, 10% citric acid, and brine
  2. customwas then evaporated
  3. washChromatography of the residue on silica gel, eluting with EtOAc/heptane

Sources & evidence

ORD record
ord-1f37653a90ca4874b0c695068ff75c89
Source dataset
uspto-grants-2013_12
Patent number
US08604205B2

Reaction notes

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