Tetrabutylammonium Fluoride → 3-(5-Hexylsulfanyl-3H-imidazol-4-yl]-pyridine

HRID 1027567Notes

Reaction equation

HRID 1027567 reaction equation
[CH2:1]([S:7][C:8]1[N:12]=[CH:11][N:10](COCC[Si](C)(C)C)[C:9]=1[C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:1]([S:7][C:8]1[N:12]=[CH:11][NH:10][C:9]=1[C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 575480793-[5-hexylsulfanyl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-imidazol-4-yl]-pyridine

Product 1

HCID 575480673-(5-Hexylsulfanyl-3H-imidazol-4-yl]-pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of anhydrous THF (30 ml) containing 74B (0.29 g, 0.74 mmol) were added 2.2 ml (3 eq) of TBAF (1.0 M in THF) under N2. After the addition, the resulting solution was refluxed for 18 hours and subsequently concentrated in vacuo. Ethyl acetate was added and the organic layer was washed with a concentrated NaHCO3 solution, dried (Na2SO4), filtered and concentrated in vacuo. The resulting residue was purified by flash chromatography (ethyl acetate) to afford 3-(5-hexylsulfanyl-3H-imidazol-4-yl)-pyridine. (77) as an oil (0.14 g, 71%). 1H-NMR (400 MHz, CDCl3): δ 9.25 (bs, 1H), 8.53 (dd, J=5 Hz, 2 Hz, 1H), 8.42-8.35 (m, 1H), 7.78 (s, 1H), 7.38-7.34 (m, 1H), 2.79-2.69 (m, 2H), 1.53-1.44 (m, 2H), 1.33-1.09 (m, 6H), 0.80 (t, J=7 Hz, 3H).

Workup

  1. additionAfter the addition
  2. temperaturethe resulting solution was refluxed for 18 hours
  3. concentrationsubsequently concentrated in vacuo
  4. additionEthyl acetate was added
  5. washthe organic layer was washed with a concentrated NaHCO3 solution
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting residue was purified by flash chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-a9ce5abd977444dda08bd3b718702bda
Source dataset
uspto-grants-2014_05
Patent number
US08735388B2

Reaction notes

Loading…