3-(Trifluoromethyl)pyrazole → 4,8-dichloro-7-methoxy-2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)quinoline

HRID 880778Notes

Reaction equation

HRID 880778 reaction equation
Cl[C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[C:5]([Cl:15])[C:6]([O:13][CH3:14])=[CH:7][CH:8]=2)[N:3]=1.[F:16][C:17]([F:24])([F:23])[C:18]1[CH:22]=[CH:21][NH:20][N:19]=1>>[Cl:12][C:10]1[C:9]2[C:4](=[C:5]([Cl:15])[C:6]([O:13][CH3:14])=[CH:7][CH:8]=2)[N:3]=[C:2]([N:20]2[CH:21]=[CH:22][C:18]([C:17]([F:24])([F:23])[F:16])=[N:19]2)[CH:11]=1

Participants

3

Reactant 2

HCID 18070343-(Trifluoromethyl)pyrazoleHCID 27945162,4,8-trichloro-7-methoxyquinoline

Product 1

HCID 566052134,8-dichloro-7-methoxy-2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)quinolineYield 51%

Conditions

Temperature
120 °C

Procedure

A mixture of compound 220d (5 g, 19 mmol) and 3-trifluoromethylpyrazole 233a (7.76 g, 57 mmol) was heated at 120° C. for 4-6 hrs and the reaction was followed by LCMS and TLC. The reaction mixture was purified by silica gel column (mono and dipyrazole were separated) using DCM and heptane as mobile phase to yield compound 235a (3.5 g) in 51% yield.

Workup

  1. customThe reaction mixture was purified by silica gel column (mono and dipyrazole were separated)

Sources & evidence

ORD record
ord-76ff47ee124b40688c5ee0fa2716e74e
Source dataset
uspto-grants-2015_03
Patent number
US08993595B2

Reaction notes

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