Water → HCID 59631198, compound

HRID 1431542Notes

Reaction equation

HRID 1431542 reaction equation
Br[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([Br:11])=[CH:4][N:3]=1.[F:12][C:13]1[C:14](B(O)O)=[CH:15][C:16]([O:19][CH3:20])=[N:17][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+].O>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:11][C:5]1[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]([C:14]2[C:13]([F:12])=[CH:18][N:17]=[C:16]([O:19][CH3:20])[CH:15]=2)=[N:3][CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2984702,5-Dibromo-3-nitropyridineHCID 44754837(5-Fluoro-2-methoxypyridin-4-yl)boronic acid

Product 1

HCID 59631198HCID 59631198, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2,5-dibromo-3-nitropyridine, commercially available from Matrix Scientific (0.72 g, 2.55 mmol), 5-fluoro-2-methoxypyridin-4-ylboronic acid, commercially available from Asymchem (0.39 g, 2.34 mmol), dichlorobis(triphenyl-phosphine)palladium (II) (90 mg, 0.13 mmol), and 1.0M sodium carbonate (3.5 mL, 7.0 mmol) in 1,4-dioxane (10 mL) was degassed by nitrogen. The mixture was heated to 90° C. After 21.5 h, the reaction was cooled to rt then treated with water. After extracting twice with EtOAc, the organic layer was combined and dried over anhydrous magnesium sulfate. After filtration and concentration, the yellowish brown residue was treated with MeOH and placed on the rotoevaporator (without vac.) in a 45° C. water bath. After 30 min, the solid was filtered and rinsed twice with MeOH to afford a tan solid as 5-bromo-5′-fluoro-2′-methoxy-3-nitro-2,4′-bipyridine. 1H NMR (500 MHz, CDCl3) δ ppm 9.01 (1H, d, J=2.0 Hz), 8.56 (1H, d, J=2.0 Hz), 8.06 (1H, d, J=1.2 Hz), 7.02 (1H, d, J=4.6 Hz), 4.04 (3H, m).

Workup

  1. temperaturethe reaction was cooled to rt
  2. extractionAfter extracting twice with EtOAc
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter filtration and concentration
  5. additionthe yellowish brown residue was treated with MeOH
  6. customplaced on the rotoevaporator (without vac.) in a 45° C.
  7. waitAfter 30 min
  8. filtrationthe solid was filtered
  9. washrinsed twice with MeOH

Sources & evidence

ORD record
ord-521579ed18bb416bb210a583e2424e6b
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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