Potassium Carbonate → 2-(2,4-Bis(trifluoromethyl)phenyl)-4-chloro-5,7-difluoro-3-methylquinoline

HRID 1431489Notes

Reaction equation

HRID 1431489 reaction equation
Cl[C:2]1[C:11]([CH3:12])=[C:10]([Cl:13])[C:9]2[C:4](=[CH:5][C:6]([F:15])=[CH:7][C:8]=2[F:14])[N:3]=1.[F:16][C:17]([F:32])([F:31])[C:18]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][C:19]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[F:16][C:17]([F:31])([F:32])[C:18]1[CH:23]=[C:22]([C:24]([F:25])([F:26])[F:27])[CH:21]=[CH:20][C:19]=1[C:2]1[C:11]([CH3:12])=[C:10]([Cl:13])[C:9]2[C:4](=[CH:5][C:6]([F:15])=[CH:7][C:8]=2[F:14])[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27826672,4-Bis(trifluoromethyl)phenylboronic acidHCID 596310402,4-Dichloro-5,7-difluoro-3-methylquinoline

Product 1

HCID 596311972-(2,4-Bis(trifluoromethyl)phenyl)-4-chloro-5,7-difluoro-3-methylquinoline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The Suzuki coupled product was prepared according to Procedure F using 2,4-dichloro-5,7-difluoro-3-methylquinoline (0.50 g, 2.02 mmol), 2,4-bis(trifluoromethyl)phenylboronic acid (0.572 g, 2.22 mmol), palladium tetrakistriphenylphosphine (0.23 g, 0.20 mmol), potassium carbonate (0.56 g, 4.03 mmol) in toluene (4 mL) at 100° C. for 22 h to give 2-(2,4-bis(trifluoromethyl)phenyl)-4-chloro-5,7-difluoro-3-methylquinoline as a crystalline solid. Mass Spectrum (ESI) m/e=426.0 (M+1).

Workup

  1. customwas prepared
  2. customat 100° C.
  3. customfor 22 h

Sources & evidence

ORD record
ord-93c01c02af384a32a3c83c90488f5dc7
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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