Dichloromethane → 4-Bromomethyl-1-(tetrahydro-pyran-2-yl)-1H-indazole

HRID 2270784Notes

Reaction equation

HRID 2270784 reaction equation
[BrH:1].BrC[C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[CH:7]2.[O:13]1[CH:18]=[CH:17][CH2:16][CH2:15][CH2:14]1.Cl[CH2:20]Cl>O1CCCC1>[Br:1][CH2:20][C:5]1[CH:4]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[N:8][N:9]2[CH:18]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 80803,4-dihydro-2H-pyranHCID 226614415-(Bromomethyl)-1H-indazole--hydrogen bromide (1/1)

Product 1

HCID 226612154-Bromomethyl-1-(tetrahydro-pyran-2-yl)-1H-indazoleYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-bromomethyl-1H-indazole hydrobromide salt (194 mg, 0.665 mmol) and 3,4-dihydro-2H-pyran (0.118 mL, 1.29 mmol) in tetrahydrofuran (4.7 mL) was heated at reflux for 2 h and then stirred overnight at room temperature. Dichloromethane (12 mL) was added and the solution was washed with aqueous sodium hydrogen carbonate, water, and brine (10 mL each), dried (MgSO4), concentrated, and chromatographed (5-60% ethyl acetate/petroleum ether) to give 4-bromomethyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (153 mg, 78%) as an off-white solid.

Workup

  1. temperatureat reflux for 2 h
  2. washthe solution was washed with aqueous sodium hydrogen carbonate, water, and brine (10 mL each)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customchromatographed (5-60% ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-c798bbe22dbb4f058b011ff7d2f160c0
Source dataset
uspto-grants-2001_12
Patent number
US06331640B1

Reaction notes

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