Potassium Carbonate → HCID 68156825, compound

HRID 1892691Notes

Reaction equation

HRID 1892691 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:9])[C:5](Cl)=[N:6][CH:7]=1.[F:10][C:11]([F:18])([F:17])[C:12]1[CH:13]=[N:14][NH:15][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([CH3:9])[C:5]([N:14]2[CH:13]=[C:12]([C:11]([F:18])([F:17])[F:10])[CH:16]=[N:15]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2854345-Bromo-2-chloro-3-methylpyridineHCID 127777954-(Trifluoromethyl)-1H-pyrazole

Product 1

HCID 68156825HCID 68156825, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
107.5 °C

Procedure

A flask was charged with 5-bromo-2-chloro-3-methylpyridine (250 mg, 1.21 mmol), 4-(trifluoromethyl)-1H-pyrazole (165 mg, 1.21 mmol), potassium carbonate (512 mg, 3.63 mmol), and anhydrous dimethylformamide (1.21 mL). The reaction was heated at 85 to 130° C. for 36 h. The reaction was concentrated to give 690 mg of crude material. Purification by silica gel flash chromatography (0-5% ethyl acetate in heptane) afforded 5-bromo-3-methyl-2-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyridine (containing approximately 30% starting material) was carried forth to the next reaction. MS (M+1) 308.1.

Workup

  1. concentrationThe reaction was concentrated
  2. customto give 690 mg of crude material
  3. customPurification by silica gel flash chromatography (0-5% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-e7c8b094a1e94d3393b033ed919eb38f
Source dataset
uspto-grants-2013_08
Patent number
US08507533B2

Reaction notes

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