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

HRID 475188Notes

Reaction equation

HRID 475188 reaction equation
[Br:1][C:2]1[C:10]2[N:9]=[CH:8][NH:7][C:6]=2[CH:5]=[CH:4][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[C:10]2[N:9]=[CH:8][N:7]([CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16][O:11]3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 112525844-Bromo-1H-benzimidazole

Product 1

HCID 712721864-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazoleYield 70.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 52 (1.30 g, 6.6 mmol) and 3,4-dihydro-2H-pyran (2.78 g, 33.0 mmol) in THF (15 mL) was added p-TsOH.H2O (0.11 g, 0.66 mmol). The mixture was stirred at 80° C. for 14 h, then the solvent was removed in vacuo. The residue was purified by SiO2 chromatography eluting with 10% petroleum ether/EtOAc to afford 1.3 g (70%) 4-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole (54) as brown oil: MS (ESI) m/z=281.0 [M+1]+.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was purified by SiO2 chromatography
  3. washeluting with 10% petroleum ether/EtOAc

Sources & evidence

ORD record
ord-c42127fd135a4fa884f96570685afa90
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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