Imidazole → HCID 71547909, compound

HRID 1497461Notes

Reaction equation

HRID 1497461 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.Br[CH:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[CH:11][N:10]=1)[CH3:8].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[N:1]1([CH:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)=[CH:11][N:10]=2)[CH3:8])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 86680628HCID 86680628, compound

Product 1

HCID 71547909HCID 71547909, compoundYield 71.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 1H-imidazole (0.069 g, 1.0 mmol) in DMF (7 mL) was added 2-(1-bromoethyl)-5-(4-methoxyphenyl)pyridine (0.150 g, 0.50 mmol) and K2CO3 (354 mg, 2.5 mmol). The reaction was heated at 50° C. for about 3 h. The reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with brine solution (10 mL), the organic layer was dried over Na2SO4 and concentrated under vacuum to obtain crude product. The crude product was purified by flash chromatography (silica gel, 100-200μ) using 2% methanol in DCM eluent to afford 2-(1-(1H-imidazol-1-yl)ethyl)-5-(4-methoxyphenyl)pyridine as an off-white solid (0.1 g, 69% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.80 (d, 1H), 7.99 (dd, 1H), 7.80 (s, 1H), 7.63 (d, 2H), 7.26 (s, 1H), 7.03 (d, 1H), 7.21 (d, 2H), 6.89 (s, 1H), 5.64-5.59 (m, 1H), 3.78 (s, 3H), 1.81 (d, 3H), LC-MS m/z calcd for [M+H]+ 280.14. found 280.2.

Workup

  1. extractionextracted with ethyl acetate (2×100 mL)
  2. washThe combined organic extracts were washed with brine solution (10 mL)
  3. dry with materialthe organic layer was dried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customto obtain crude product
  6. customThe crude product was purified by flash chromatography (silica gel, 100-200μ)

Sources & evidence

ORD record
ord-a63d02aae2994835bf08428dc70e22b5
Source dataset
uspto-grants-2015_12
Patent number
US09199975B2

Reaction notes

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