Potassium Carbonate → 4-Chloro-5,7-difluoro-3-methyl-2-(6-(piperidin-1-yl)pyridin-3-yl)quinoline

HRID 1431719Notes

Reaction equation

HRID 1431719 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.[N:16]1([C:22]2[N:27]=[CH:26][C:25](B3OC(C)(C)C(C)(C)O3)=[CH:24][CH:23]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.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:25]2[CH:26]=[N:27][C:22]([N:16]3[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]3)=[CH:23][CH:24]=2)[C:11]=1[CH3:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 164142101-[5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl]piperidineHCID 596310402,4-Dichloro-5,7-difluoro-3-methylquinoline

Product 1

HCID 596310544-Chloro-5,7-difluoro-3-methyl-2-(6-(piperidin-1-yl)pyridin-3-yl)quinoline

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), 6-(piperidin-1-yl)pyridine-3-boronic acid pinacol ester (0.581 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 18 h to give 4-chloro-5,7-difluoro-3-methyl-2-(6-(piperidin-1-yl)pyridin-3-yl)quinoline as a yellow solid. Mass Spectrum (ESI) m/e=374.0 (M+1).

Workup

  1. customwas prepared
  2. customat 100° C.
  3. customfor 18 h

Sources & evidence

ORD record
ord-0721ff2336a9406a9b158f2ef74ecb3e
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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