2,3-Dichloropyridine → 3-Chloro-2-(3-chloro-pyrazol-1-YL)-pyridine

HRID 475458Notes

Reaction equation

HRID 475458 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:9][C:10]1[CH:14]=[CH:13][NH:12][N:11]=1.[K].C(=O)([O-])[O-]>CN(C)C=O>[Cl:8][C:7]1[C:2]([N:12]2[CH:13]=[CH:14][C:10]([Cl:9])=[N:11]2)=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 169882,3-DichloropyridineHCID 19660Carbonate IonHCID 5462222PotassiumHCID 178478253HCID 178478253, compound2×

Product 1

HCID 228315663-Chloro-2-(3-chloro-pyrazol-1-YL)-pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 2,3-dichloropyridine (92.60 g, 0.629 mol) and 3-chloropyrazole (i.e. the product of Step B) (64.44 g, 0.629 mol) in N,N-dimethylformamide (400 mL) was added potassium, carbonate (147.78 g, 1.06 mol), and the reaction mixture was then heated to 100° C. for 36 hours. The reaction mixture was cooled to room temperature and slowly poured into ice water. The precipitated solids were altered and washed with water. The solid filter cake was taken up in ethyl acetate, dried over magnesium sulfate and concentrated. The crude solid was chromatographed on silica gel using 20% ethyl acetate/hexane as eluent to afford the title product as a white solid (39.75 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with water
  3. filtrationThe solid filter cake
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe crude solid was chromatographed on silica gel using 20% ethyl acetate/hexane as eluent

Sources & evidence

ORD record
ord-514b7180d7ad41cc9b17d54ba39c628a
Source dataset
uspto-grants-2014_01
Patent number
US08637552B2

Reaction notes

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