2-Fluoro-6-(1h-imidazol-2-yl)pyridine → HCID 22260382, compound

HRID 1609831Notes

Reaction equation

HRID 1609831 reaction equation
Cl[CH2:2][C:3]1[C:8]([O:9][CH2:10][CH3:11])=[CH:7][C:6]([O:12][CH2:13][CH3:14])=[CH:5][N:4]=1.[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]2[NH:23][CH:24]=[CH:25][N:26]=2)[N:17]=1>CN(C=O)C.O>[F:15][C:16]1[N:17]=[C:18]([C:22]2[N:26]([CH2:2][C:3]3[C:8]([O:9][CH2:10][CH3:11])=[CH:7][C:6]([O:12][CH2:13][CH3:14])=[CH:5][N:4]=3)[CH:25]=[CH:24][N:23]=2)[CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 219192862-Fluoro-6-(1h-imidazol-2-yl)pyridineHCID 22260384HCID 22260384, compound

Product 1

HCID 22260382HCID 22260382, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloromethyl-3,5-diethoxy-pyridine (174 mg, 0.69 mmol) in DMF (5 mL) is added 2-fluoro-6-(1H-imidazol-2-yl)-pyridine (112 mg, 0.69 mmol), and the reaction is stirred at room temperature overnight. The reaction mixture is diluted with water, extracted with EtOAc, washed with brine, dried over Na2SO4, and concentrated. The residue is purified by column chromatography eluting with 8% MeOH—CH2Cl2 containing few drops of NH4OH to afford 2-[2-(6-fluoro-pyridin-2-yl)-imidazol-1-yl methyl]-3,5-diethoxy-pyridine (118 mg, 49%); 1H NMR (300 MHz, CDCl3): 8.06 (dd, J=5.1, 2.4 Hz, 1H), 7.81 (t, J=7.9 Hz, 1H), 7.75 (d, J=2.4 Hz, 1H), 7.09 (s, 1H), 7.04 (s, 1H), 6.80 (dd, J=5.1, 2.7 Hz, 1H), 6.65 (d, J=2.4 Hz, 1H), 5.95 (s, 2H), 4.02 (q, J=6.9 Hz, 2H), 3.90 (q, J=6.9 Hz, 2H), 1.39 (t, J=6.9 Hz, 2H), 1.16 (t, J=6.9 Hz, 2H), m/z 343 [M+1].

Workup

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue is purified by column chromatography
  6. washeluting with 8% MeOH—CH2Cl2 containing few drops of NH4OH

Sources & evidence

ORD record
ord-ec9b3d1e856e4d54a1c09d879013ff99
Source dataset
uspto-grants-2006_01
Patent number
US06982268B2

Reaction notes

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