Potassium Carbonate → 3-Chloro-2-(3-chloro-pyrazol-1-YL)-pyridine

HRID 61939Notes

Reaction equation

HRID 61939 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.C(=O)([O-])[O-].[K+].[K+]>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

5

Reactant 3

HCID 11430Potassium CarbonateHCID 169882,3-DichloropyridineHCID 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 filtered 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. filtrationThe precipitated solids were filtered
  3. washwashed with water
  4. filtrationThe solid filter cake
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe crude solid was chromatographed on silica gel using 20% ethyl acetate/hexane as eluent

Sources & evidence

ORD record
ord-cbd86a22a5514b1a91de90c2e48b4e44
Source dataset
uspto-grants-2016_09
Patent number
US09445593B1

Reaction notes

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