Imidazole → HCID 59191303, compound

HRID 1023930Notes

Reaction equation

HRID 1023930 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].Cl[CH2:9][C:10]1[CH:23]=[CH:22][C:13]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[N:16]=2)=[C:12]([O:24][CH3:25])[CH:11]=1>CN(C=O)C>[F:21][C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([O:14][C:13]2[CH:22]=[CH:23][C:10]([CH2:9][N:1]3[CH:5]=[CH:4][N:3]=[CH:2]3)=[CH:11][C:12]=2[O:24][CH3:25])[N:16]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 59191250HCID 59191250, compound

Product 1

HCID 59191303HCID 59191303, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
40 °C

Procedure

To a solution of imidazole (18 mg; 0.27 mmol) and NaH (12 mg; 0.30 mmol) in DMF (1 mL), under argon, was added a solution of 2-[4-(chloromethyl)-2-methoxyphenoxy]-6-fluoropyridine (65 mg; 0.24 mmol) in DMF (1 mL). The reaction mixture was allowed to stir overnight, to 40° C. After concentration, the reaction was hydrolysed with saturated NH4Cl (1 mL), extracted with AcOEt (2*1 mL). Combined organic phases were dried over Na2SO4, concentrated in vacuo, the title compound (68 mg; 93%) was obtained.

Workup

  1. concentrationAfter concentration
  2. extractionextracted with AcOEt (2*1 mL)
  3. dry with materialCombined organic phases were dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e20f85172f69429da21c19dd99018fcb
Source dataset
uspto-grants-2014_05
Patent number
US08722746B2

Reaction notes

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