Sodium Carbonate → HCID 59631229, compound

HRID 1431549Notes

Reaction equation

HRID 1431549 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.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>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:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[O:13][CH3:12])=[N:3][CH:4]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2984702,5-Dibromo-3-nitropyridineHCID 27339582-Methoxyphenylboronic acid

Product 1

HCID 59631229HCID 59631229, 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 (0.533 g, 1.89 mmol), 2-methoxyphenylboronic acid (0.29 g, 1.91 mmol), trans-dichlorobis(triphenylphosphine)-palladium (II) (68.9 mg, 0.098 mmol), and 2.0M sodium carbonate (2.9 mL, 5.8 mmol) in 1,4-dioxane (6 mL) was degassed by nitrogen. The mixture was heated to 90° C. After 7 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 residue was purified on silica gel (0-15% EtOAc in hexanes) to afford a yellow solid as 5-bromo-2-(2-methoxyphenyl)-3-nitropyridine. 1H NMR (400 MHz, CDCl3) δ ppm 8.93 (1H, d, J=2.2 Hz), 8.37 (1H, d, J=2.0 Hz), 7.66 (1H, dd, J=7.6, 1.8 Hz), 7.51 (1H, m), 7.16 (1H, td, J=7.5, 1.0 Hz), 6.92 (1H, dd, J=8.3, 0.9 Hz), 3.72 (3H, s).

Workup

  1. customwas degassed by nitrogen
  2. temperaturethe reaction was cooled to rt
  3. additiontreated with water
  4. extractionAfter extracting twice with EtOAc
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtration and concentration the residue
  7. customwas purified on silica gel (0-15% EtOAc in hexanes)

Sources & evidence

ORD record
ord-678092f8ebc844d5a5bdddcf09047404
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

Loading…