Imidazole → HCID 71547823, compound

HRID 1497434Notes

Reaction equation

HRID 1497434 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH:13]([C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=2)=[CH:18][N:17]=1)[CH2:14][CH3:15]>CN(C=O)C.O>[N:1]1([CH:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=3)=[CH:18][N:17]=2)[CH2:14][CH3:15])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 86680609HCID 86680609, compound

Product 1

HCID 71547823HCID 71547823, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of imidazole (0.2 g, 2.9 mmol) in DMF (5 mL) was added potassium carbonate (0.4 g, 2.9 mmol) and 2-(1-bromopropyl)-5-(3-methoxyphenyl)pyridine under nitrogen and the reaction was heated to 50° C. for 3 h. The contents were cooled to rt, diluted with water (100 mL) and extracted with ethyl acetate (2×100 mL). The layers were separated, the organic layer was washed with brine solution (2×30 mL), dried over sodium sulphate and distilled off to get the crude product. The product was purified by preparative TLC (2000μ; pure ethyl acetate) to provide 2-(1-(1H-imidazol-1-yl)propyl)-5-(3-methoxyphenyl)pyridine (50 mg, 12% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.86 (s, 1H), 8.09 (d, 1H), 7.81 (s, 1H), 7.40 (m, 2H), 7.36 (s, 1H), 7.25 (d, 2H), 6.97 (d, 1H), 6.89 (s, 1H), 5.37 (q, 1H), 3.80 (s, 3H), 2.25 (m, 2H), 0.82 (t, 3H); LC-MS m/z calcd for [M+H]+ 294.15. found 294.2.

Workup

  1. temperatureThe contents were cooled to rt
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. customThe layers were separated
  4. washthe organic layer was washed with brine solution (2×30 mL)
  5. dry with materialdried over sodium sulphate
  6. distillationdistilled off
  7. customto get the crude product
  8. customThe product was purified by preparative TLC (2000μ; pure ethyl acetate)

Sources & evidence

ORD record
ord-4af2acb387704f84918c2b3c9b372f8a
Source dataset
uspto-grants-2015_12
Patent number
US09199975B2

Reaction notes

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