Cesium carbonate → HCID 57516327, compound

HRID 1753210Notes

Reaction equation

HRID 1753210 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]([F:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH3:14]B1OB(C)OB(C)O1.C(=O)([O-])[O-].[Cs+].[Cs+]>O.ClCCl.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[Cl:1][C:2]1[N:11]=[C:10]([CH3:14])[C:9]([F:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 574072TrimethylboroxineHCID 2775354Methyl 2,6-dichloro-5-fluoronicotinate

Product 1

HCID 57516327HCID 57516327, compoundYield 25.2%

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of methyl 2,6-dichloro-5-fluoronicotinate (17) (3.5 g 15.62 mmol), trimethylboroxin (1.96 g, 15.62 mmol), 1,1′-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane (1.276 g, 1.562 mmol) and cesium carbonate 15.27 g, 46.86 mmol) was heated at 110° C. overnight. The mixture is cooled to room temperature, diluted with water, and extracted with EtOAc. The combined organic phase is washed with water followed by brine, then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue is purified by flash silica gel chromatography using a gradient of 0-30% EtOAc/heptanes to provide methyl 2-chloro-5-fluoro-6-methylnicotinate (18) 0.8 g as a colorless solid (0.8 g 25%).

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. extractionextracted with EtOAc
  3. washThe combined organic phase is washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-3beb37fa09cd41ba9c0331d9dba64f61
Source dataset
uspto-grants-2015_10
Patent number
US09163020B2

Reaction notes

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