Sodium Carbonate → HCID 67285562, compound

HRID 1618688Notes

Reaction equation

HRID 1618688 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.[F:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[N:21][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(Cl)Cl.O>[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:19]2[CH:20]=[N:21][CH:22]=[C:17]([F:16])[CH:18]=2)[C:11]=1[CH3:12]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 44717403(5-Fluoropyridin-3-yl)boronic acidHCID 596310402,4-Dichloro-5,7-difluoro-3-methylquinoline

Product 1

HCID 67285562HCID 67285562, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Prepared according to procedure F by stirring 2,4-dichloro-5,7-difluoro-3-methylquinoline (1 g, 4.03 mmol), 5-fluoropyridine-3-boronic acid (0.568 g, 4.03 mmol), PdCl2(PPh3)2 (0.283 g, 0.403 mmol), sodium carbonate (0.505 mL, 12.09 mmol), 1,4-dioxane (5 mL), and water (1.25 mL) at 95° C. for 3 h. Trituration of the crude product with DCM afforded 4-chloro-5,7-difluoro-2-(5-fluoropyridin-3-yl)-3-methylquinoline. Mass Spectrum (ESI) m/e=309.0 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-4fd25d3ddeac4473823581634ca1c8c7
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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