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

HRID 925962Notes

Reaction equation

HRID 925962 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-trifluoromethyl)pyrazole 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-8f8487b4c2104cff861dbaabcb3abe92
Source dataset
uspto-grants-2016_03
Patent number
US09284307B2

Reaction notes

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