Sodium Carbonate → 4-Methyl-5-nitro-2,3'-bipyridine

HRID 1774949Notes

Reaction equation

HRID 1774949 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.C([O-])([O-])=O.[Na+].[Na+].[N:18]1[CH:23]=[CH:22][CH:21]=[C:20](B(O)O)[CH:19]=1>CN(C=O)C.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]>[CH3:8][C:6]1[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=[C:2]([C:20]2[CH:19]=[N:18][CH:23]=[CH:22][CH:21]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 3458732-Bromo-4-methyl-5-nitropyridineHCID 27343783-Pyridinylboronic acid

Product 1

HCID 463160084-Methyl-5-nitro-2,3'-bipyridineYield 80%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-bromo-4-methyl-5-nitropyridine (217 g, 1 mol) in DMF (2000 mL) was added Pd(dppf)Cl2 (5 g), saturated solution of Na2CO3 (200 mL) and pyridin-3-ylboronic acid (147 g, 1.2 mol). The mixture was stirred under argon for 6 h at 100. After cooling down, the solvent was removed under reduced pressure evaporation and the residue was purified by silica-gel column chromatography (mobile phase: EA:PE=1:1) to afford 4-methyl-5-nitro-2,3′-bipyridine (172 g, 80%).

Workup

  1. temperatureAfter cooling down
  2. customthe solvent was removed under reduced pressure evaporation
  3. customthe residue was purified by silica-gel column chromatography (mobile phase: EA:PE=1:1)

Sources & evidence

ORD record
ord-8932df7d762e40b78c799fcf4326575a
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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