Potassium Carbonate → 4-Chloro-2-(3,5-difluorophenyl)-3-methyl-1,8-naphthyridine

HRID 1618739Notes

Reaction equation

HRID 1618739 reaction equation
Cl[C:2]1[C:11]([CH3:12])=[C:10]([Cl:13])[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[F:14][C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[C:19]([F:21])[CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.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>[Cl:13][C:10]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([C:17]2[CH:16]=[C:15]([F:14])[CH:20]=[C:19]([F:21])[CH:18]=2)[C:11]=1[CH3:12]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2734338(3,5-Difluorophenyl)boronic acidHCID 220826612,4-Dichloro-3-methyl-1,8-naphthyridine

Product 1

HCID 596315174-Chloro-2-(3,5-difluorophenyl)-3-methyl-1,8-naphthyridine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Prepared according to procedure F using 2,4-dichloro-3-methyl-1,8-naphthyridine (0.4 g, 1.877 mmol), 3,5-difluorophenylboronic acid (0.445 g, 2.82 mmol), Pd(PPh3)4 (0.217 g, 0.188 mmol), potassium carbonate (0.519 g, 3.75 mmol) in toluene (6 mL) at 95° C. for 18 h. Purification by column chromatography (silica gel; 0-25% EtOAc in hexanes) gave 4-chloro-2-(3,5-difluorophenyl)-3-methyl-1,8-naphthyridine as a yellow amorphous solid. Mass Spectrum (ESI) m/e=291.0 (M+1).

Workup

  1. customPrepared
  2. customat 95° C.
  3. customfor 18 h
  4. customPurification by column chromatography (silica gel; 0-25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-a4ab91fb07d7497e8045a8876a340967
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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