3,4-dihydro-2H-pyran → HCID 71272225, compound

HRID 475102Notes

Reaction equation

HRID 475102 reaction equation
[Br:1][C:2]1[C:10]([CH3:11])=[CH:9][C:5]2[NH:6][CH:7]=[N:8][C:4]=2[CH:3]=1.[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1>C1COCC1.CC1C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[C:10]([CH3:11])=[CH:9][C:5]2[N:6]([CH:13]3[CH2:14][CH2:15][CH2:16][CH2:17][O:12]3)[CH:7]=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 207849005-Bromo-6-methyl-1H-benzimidazole

Product 1

HCID 71272225HCID 71272225, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-bromo-6-methyl-1H-benzo[d]imidazole (2.0 g, 9.6 mmol), p-TsOH (17 mg, 0.1 mmol), and dihydropyran (8.1 g, 96 mmol) in THF (30 mL) was heated to reflux overnight. The solvent was concentrated in vacuo and EtOAc (50 mL) and water (50 mL) were added to the residue. The pH was adjusted to about 8 with K2CO3. The aqueous phase was extracted with EtOAc (50 mL×2). The combined organic layers were washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by SiO2 chromatography eluting with petroleum ether/EtOAc (2:1) to afford 5-bromo-6-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole as a yellow solid (2.1 g, 71%). MS (ESI): m/z=295.2 [M+1]+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. concentrationThe solvent was concentrated in vacuo and EtOAc (50 mL) and water (50 mL)
  4. additionwere added to the residue
  5. extractionThe aqueous phase was extracted with EtOAc (50 mL×2)
  6. washThe combined organic layers were washed with water and brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by SiO2 chromatography
  11. washeluting with petroleum ether/EtOAc (2:1)

Sources & evidence

ORD record
ord-d142ec1f74ca48c1bbd86e2e33a98a57
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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