Potassium Carbonate → 5-(4-chloro-5,7-difluoro-3-methylquinolin-2-yl)-N,N-dimethylpyridin-2-amine

HRID 1431521Notes

Reaction equation

HRID 1431521 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.O.[CH3:17][N:18]([C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][N:21]=1)[CH3:19].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[Cl:13][C:10]1[C:9]2[C:4](=[CH:5][C:6]([F:15])=[CH:7][C:8]=2[F:14])[N:3]=[C:2]([C:23]2[CH:24]=[CH:25][C:20]([N:18]([CH3:19])[CH3:17])=[N:21][CH:22]=2)[C:11]=1[CH3:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 441190932-(Dimethylamino)pyridine-5-boronic acid hydrateHCID 596310402,4-Dichloro-5,7-difluoro-3-methylquinoline

Product 1

HCID 596310435-(4-chloro-5,7-difluoro-3-methylquinolin-2-yl)-N,N-dimethylpyridin-2-amine

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-(N,N-dimethylamino)pyridine-5-boronic acid hydrate (0.335 g, 2.02 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 1.3 h to give 5-(4-chloro-5,7-difluoro-3-methylquinolin-2-yl)-N,N-dimethylpyridin-2-amine as a yellow solid. Mass Spectrum (ESI) m/e=344.1 (M+1).

Workup

  1. customwas prepared
  2. customat 100° C.
  3. customfor 1.3 h

Sources & evidence

ORD record
ord-afa0416bc4f24241b1ca06ad7d44b528
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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