Potassium Carbonate → HCID 59631183, compound

HRID 1431413Notes

Reaction equation

HRID 1431413 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.[NH:16]1[C:24]2[C:19](=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH: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:20]2[CH:21]=[CH:22][CH:23]=[C:24]3[C:19]=2[CH:18]=[CH:17][NH:16]3)[C:11]=1[CH3:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27631731H-Indole-4-boronic acidHCID 596310402,4-Dichloro-5,7-difluoro-3-methylquinoline

Product 1

HCID 59631183HCID 59631183, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 2,4-dichloro-5,7-difluoro-3-methylquinoline (1.0 g, 4.03 mmol) in toluene (8.06 mL) was added 1H-indol-4-ylboronic acid (0.973 g, 6.05 mmol), potassium carbonate (1.671 g, 12.1 mmol) and palladium tetrakistriphenylphosphine (0.466 g, 0.403 mmol). The reaction was stirred at 100° C. and stirring continued for 19 h. The reaction mixture was cooled to rt and concentrated in vacuo. The crude product was placed in DCM and filtered to give the desired product. The filtrate was purified by column chromatography on silica gel, eluting with 0-50% EtOAc in hexanes to provide 4-chloro-5,7-difluoro-2-(1H-indol-4-yl)-3-methylquinoline as a yellow solid. Mass Spectrum (ESI) m/e=329.0 (M+1).

Workup

  1. stirringstirring
  2. temperatureThe reaction mixture was cooled to rt
  3. concentrationconcentrated in vacuo
  4. filtrationfiltered

Sources & evidence

ORD record
ord-1080d1bed35a432d9b59527555631339
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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