Methyl 5-bromo-2-chloronicotinate → HCID 68008409, compound

HRID 533145Notes

Reaction equation

HRID 533145 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH:13]([B-](F)(F)F)=[CH2:14].[K+]>CCO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:10][O:9][C:7](=[O:8])[C:6]1[CH:11]=[C:2]([Br:1])[CH:3]=[N:4][C:5]=1[CH:13]=[CH2:14]

Participants

5

Reactant 2

HCID 2763343Methyl 5-bromo-2-chloronicotinateHCID 23679353Potassium vinyltrifluoroborate

Product 1

HCID 68008409HCID 68008409, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 5-bromo-2-chloronicotinate (500 mg, 2.0 mmol) was dissolved in EtOH (20 mL) with potassium vinyltrifluoroborate (269 mg, 2.0 mmol), TEA (0.28 mL, 2.0 mmol), and [1,1′-Bis (diphenylphosphino)ferrocene]dichloropalladium(II) (PdCl2(dppf)) (29 mg, 0.04 mmol). The reaction was heated at 80° C. for 1 h, filtered through a Celite pad. The filtrate was concentrated, partitioned between EtOAc (50 mL) and H2O (50 mL). The organic layer was separated, dried over MgSO4 and concentrated. Purification over silica gel using automated flash chromatography (EtOAc/hexanes 0-20%) affords the compound, methyl-5-bromo-2-vinylnicotinate, as a white solid (484 mg, 76%). LC-MS (M+H)=242.1.

Workup

  1. filtrationfiltered through a Celite pad
  2. concentrationThe filtrate was concentrated
  3. custompartitioned between EtOAc (50 mL) and H2O (50 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customPurification over silica gel using automated flash chromatography (EtOAc/hexanes 0-20%)

Sources & evidence

ORD record
ord-fddfa0fbe793432fa1738d92589172dc
Source dataset
uspto-grants-2014_10
Patent number
US08853237B2

Reaction notes

Loading…