Water → HCID 67499429, compound

HRID 2408178Notes

Reaction equation

HRID 2408178 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][NH:4][N:3]=1.[H-].[Na+].F[C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1.O>CN(C)C=O>[CH3:1][C:2]1[CH:6]=[CH:5][N:4]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[N:3]=1.[CH3:1][C:2]1[N:3]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[N:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 677943-FluoropyridineHCID 178428694HCID 178428694, compound

Product 2

HCID 67499429HCID 67499429, compoundYield 51.2%HCID 67499863HCID 67499863, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-methyl-1H-pyrazole (10.99 g, 134 mmol) in N,N-dimethylformamide (100 ml) at 0° C. was added sodium hydride (3.71 g, 154 mmol, 60% dispersion). The reaction was stirred at 0° C. for 2 hours. 3-Fluoropyridine (10.0 g, 103 mmol) was added, and the reaction was stirred at 100° C. overnight. The reaction was cooled to room temperature and water was added slowly. The mixture was extracted with dichloromethane and the combined organic phases were washed with brine, concentrated and chromatographed (0-100% ethyl acetate/hexanes) to afford 3-(3-methyl-1H-pyrazol-1-yl)pyridine (8.4 g, 52.77 mmol, 51.2%) and 3-(5-methyl-1H-pyrazol-1-yl)pyridine (1.0 g, 6%). Analytical data of both products is consistent with that reported under Example 6, Step 1.

Workup

  1. stirringthe reaction was stirred at 100° C. overnight
  2. temperatureThe reaction was cooled to room temperature
  3. extractionThe mixture was extracted with dichloromethane
  4. washthe combined organic phases were washed with brine
  5. concentrationconcentrated
  6. customchromatographed (0-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-d9fcfe94c6f94eec8517ae4c8ffe81fc
Source dataset
uspto-grants-2014_08
Patent number
US08815271B2

Reaction notes

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