Toluene → HCID 67285680, compound

HRID 1618668Notes

Reaction equation

HRID 1618668 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.[C:16]1(/[CH:22]=[CH:23]/B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+].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.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](/[CH:23]=[CH:22]/[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11]=1[CH3:12]

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 5702628Styrylboronic acidHCID 596310402,4-Dichloro-5,7-difluoro-3-methylquinoline

Product 1

HCID 67285680HCID 67285680, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

Prepared according to procedure F by stirring 2,4-dichloro-5,7-difluoro-3-methylquinoline (700 mg, 2.82 mmol), trans-2-phenylvinylboronic acid (501 mg, 3.39 mmol), Pd(PPh3)4 (245 mg, 0.212 mmol), sodium carbonate (0.590 mL, 14.11 mmol), toluene (23 mL), and water (6 mL) at 95° C. for 18 h. Purification by column chromatography (silica gel, 0-10% EtOAc in hexanes as eluent) gave (E)-4-chloro-5,7-difluoro-3-methyl-2-styrylquinoline. Mass Spectrum (ESI) m/e=316.0 (M+1).

Workup

  1. customPrepared
  2. customPurification by column chromatography (silica gel, 0-10% EtOAc in hexanes as eluent)

Sources & evidence

ORD record
ord-352978b36e624b97b8eda4453ff53403
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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