Dichloromethane → HCID 86675621, compound

HRID 1844571Notes

Reaction equation

HRID 1844571 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[C:6]([CH2:8][C:9]#[N:10])[N:5]=[CH:4]1.F[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.C(Cl)Cl>CN(C)C=O>[N:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[N:3]1[CH:7]=[C:6]([CH2:8][C:9]#[N:10])[N:5]=[CH:4]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 97462-FluoropyridineHCID 24758Sodium hydrideHCID 178510863HCID 178510863, compound

Product 1

HCID 86675621HCID 86675621, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

Sodium hydride (63% mineral oil dispersion, 4.71 g) was added over 15 minutes to a solution of 1H-imidazol-4-ylacetonitrile (13.25 g) in N,N-dimethylformamide (46 mL) cooled to 0° C. Then, a solution of 2-fluoropyridine (12.61 g) in N,N-dimethylformamide (23 mL) was added thereto at room temperature, and the mixture was stirred at 100° C. for 5 hours. To the reaction solution, ice water was added, and methylene chloride was added. The formed solid was removed by suction filtration, and the organic layer was then separated and dried over anhydrous magnesium sulfate. Volatile matter was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the title compound (18.5 g, mixture with N,N-dimethylformamide).

Workup

  1. customThe formed solid was removed by suction filtration
  2. customthe organic layer was then separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationVolatile matter was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-39f51d52edd94e8ebbac12d7431277ed
Source dataset
uspto-grants-2015_02
Patent number
US08946443B2

Reaction notes

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