Water → HCID 58551572, compound

HRID 1908038Notes

Reaction equation

HRID 1908038 reaction equation
[Cl:1][C:2]1[C:7](F)=[CH:6][CH:5]=[CH:4][N:3]=1.[NH:9]1[CH:13]=[CH:12][CH:11]=[N:10]1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Cl:1][C:2]1[C:7]([N:9]2[CH:13]=[CH:12][CH:11]=[N:10]2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 27827912-Chloro-3-fluoropyridine

Product 1

HCID 58551572HCID 58551572, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-chloro-3-fluoro-pyridine (1.3 g, 10.0 mmol), 1H-pyrazole (749 mg, 11.0 mmol) and K2CO3 (4.1 g, 30.0 mmol) was stirred in DMF (15 mL) at 80° C. for 16 hours. The reaction mixture was poured into water and extracted with EtOAc (3×). The organics were combined, washed with water (3×), brine, dried (Na2SO4) and evaporated to dryness. Purification by column chromatography (5 to 30% EtOAc in hexanes) gave the desired product (0.7 g, 40%) as a white solid. ESI-MS m/z calc. 179.3. found 180.3 (M+1)+. Retention time: 0.74 minutes (3 min run).

Workup

  1. extractionextracted with EtOAc (3×)
  2. washwashed with water (3×), brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated to dryness
  5. customPurification by column chromatography (5 to 30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-cec70804ed0f470aadbb2f31a27799d4
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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