Cesium carbonate → HCID 67513659, compound

HRID 1508525Notes

Reaction equation

HRID 1508525 reaction equation
[Cl:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[F:14][C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][C:20]=1[O:21][CH3:22].C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1>[Cl:1][C:2]1[CH:12]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:5]=[N:4][C:3]=1[C:17]1[CH:18]=[CH:19][C:20]([O:21][CH3:22])=[C:15]([F:14])[CH:16]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27821943-Fluoro-4-methoxyphenylboronic acidHCID 16762519Ethyl 5,6-Dichloronicotinate

Product 1

HCID 67513659HCID 67513659, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 5,6-dichloronicotinate (1 g, 4.54 mmol), 3-fluoro-4-methoxyphenylboronic acid (0.965 g, 5.68 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.371 g, 0.454 mmol), cesium carbonate (3.26 g, 10.00 mmol) and THF (30 mL) were refluxed in an 80° C. oil bath under N2 for 2.5 hrs. Volatiles were removed under reduced pressure. The pot residue was worked up with brine, extracted with ethyl acetate, dried over Na2SO4, filtered and evaporated to afford a dark mixture. The resulting crude mixture was purified by flash chromatography (SiO2, Biotage 65i cartridge). The column was eluted by an EtOAc/hexanes mixture (0% to 40%). Related fractions were pooled and evaporated to afford a white fluffy solid as the titled compound. LCMS calc.=309.06. found=310.01 (M+H)+.

Workup

  1. customVolatiles were removed under reduced pressure
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customto afford a dark mixture
  7. customThe resulting crude mixture was purified by flash chromatography (SiO2, Biotage 65i cartridge)
  8. washThe column was eluted by an EtOAc/hexanes mixture (0% to 40%)
  9. customevaporated

Sources & evidence

ORD record
ord-52480f1b07e84569a3c78163b5140062
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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