3,4-dihydro-2H-pyran → 5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole

HRID 475201Notes

Reaction equation

HRID 475201 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]2[NH:6][CH:7]=[N:8][C:4]=2[CH:3]=1.[O:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1.CC1C=CC(S(O)(=O)=O)=CC=1.O>C1COCC1>[Br:1][C:2]1[CH:10]=[CH:9][C:5]2[N:6]([CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16][O:11]3)[CH:7]=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 178419331HCID 178419331, compound

Product 1

HCID 672932855-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazoleYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 78 (4.5 g, 23 mmol), 3,4-dihydro-2H-pyran (9 mL, 0.1 mol), p-TsOH.H2O (1.0 g, 3.4 mmol) in THF (200 mL) was stirred under nitrogen at 80° C. for 18 h. The reaction mixture was concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with DCM/MeOH (100:1) to afford 6.0 g (100%) of 5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole (80) as yellow oil: MS (ESI) m/z=281.0 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe crude product was purified by SiO2 chromatography
  3. washeluting with DCM/MeOH (100:1)

Sources & evidence

ORD record
ord-bc738657f184418aba39653dbd6ba09b
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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