Potassium Carbonate → HCID 59631536, compound

HRID 1431738Notes

Reaction equation

HRID 1431738 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.[CH3:16][N:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:28]=[C:27](B3OC(C)(C)C(C)(C)O3)[CH:26]=[CH:25][N:24]=2)[CH2:19][CH2:18]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:27]2[CH:26]=[CH:25][N:24]=[C:23]([N:20]3[CH2:19][CH2:18][N:17]([CH3:16])[CH2:22][CH2:21]3)[CH:28]=2)[C:11]=1[CH3:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27695372-(4-Methylpiperazin-1-yl)pyridine-4-boronic acid, pinacol esterHCID 596310402,4-Dichloro-5,7-difluoro-3-methylquinoline

Product 1

HCID 59631536HCID 59631536, compound

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, 2.0 mmol), 1-methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine (0.61 g, 2.02 mmol), palladium tetrakistriphenylphosphine (0.23 g, 0.20 mmol), potassium carbonate (0.56 g, 4.0 mmol) in toluene (4.0 mL) at 100° C. for 22 h to give 4-chloro-5,7-difluoro-3-methyl-2-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)quinoline as a light yellow solid. Mass Spectrum (ESI) m/e=389.1 (M+1).

Workup

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

Sources & evidence

ORD record
ord-de8632ac127246df80476f7a04e636db
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

Loading…