Potassium Carbonate → HCID 59631439, compound

HRID 1618719Notes

Reaction equation

HRID 1618719 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:23]=[C:22](B(O)O)[CH:21]=[CH:20][N:19]=1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.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]=[CH:20][N:19]=[C:18]([O:17][CH3:16])[CH:23]=2)[C:11]=1[CH3:12]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 23546919(2-Methoxypyridin-4-yl)boronic acidHCID 596310402,4-Dichloro-5,7-difluoro-3-methylquinoline

Product 1

HCID 59631439HCID 59631439, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Prepared according to procedure F by stirring 2,4-dichloro-5,7-difluoro-3-methylquinoline (0.5 g, 2.02 mmol), 2-methoxypyridin-4-ylboronic acid (0.31 g, 2.02 mmol), potassium carbonate (0.56 g, 4.03 mmol), Pd(PPh3)4 (0.23 g, 0.20 mmol), and toluene (4 mL) at 100° C. for 18 h. Purification by column chromatography (silica gel, 0-30% EtOAc in hexanes) gave 4-chloro-5,7-difluoro-2-(2-methoxypyridin-4-yl)-3-methylquinoline as an off-white solid. Mass Spectrum (ESI) m/e=321.1 (M+1).

Workup

  1. customPrepared
  2. customPurification by column chromatography (silica gel, 0-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-51cadb1347d64ddf8722789fa33cc9f7
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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