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

HRID 420081Notes

Reaction equation

HRID 420081 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 45d (5 g, 19 mmol) and 3-trifluoromethylpyrazole 86a (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 119b (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-c38cac5e0432456aac828bda7a786016
Source dataset
uspto-grants-2012_01
Patent number
US08093379B2

Reaction notes

Loading…