Potassium Carbonate → HCID 66632601, compound

HRID 1431526Notes

Reaction equation

HRID 1431526 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][O:17][C:18]1[CH:19]=[N:20][CH:21]=[C:22](B2OC(C)(C)C(C)(C)O2)[CH:23]=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:22]2[CH:21]=[N:20][CH:19]=[C:18]([O:17][CH3:16])[CH:23]=2)[C:11]=1[CH3:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 38661613-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 596310402,4-Dichloro-5,7-difluoro-3-methylquinoline

Product 1

HCID 66632601HCID 66632601, 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 (0.35 g, 1.4 mmol), 3-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.50 g, 2.12 mmol), palladium tetrakistriphenylphosphine (0.16 g, 0.14 mmol), potassium carbonate (0.49 g, 4.23 mmol) in toluene (2.8 mL) at 100° C. for 17.6 h to give 4-chloro-5,7-difluoro-2-(5-methoxypyridin-3-yl)-3-methylquinoline as a white solid. Mass Spectrum (ESI) m/e=321.0 (M+1).

Workup

  1. customwas prepared
  2. customat 100° C.
  3. customfor 17.6 h

Sources & evidence

ORD record
ord-c6bdfb972ea94cc482115e247ec4bd79
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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