Sodium Carbonate → 2-Methyl-3-nitro-6-phenylpyridine

HRID 849405Notes

Reaction equation

HRID 849405 reaction equation
Cl.BrC1C=CC2N(CC3N=CNC=3)CC[N:9]([C:19]([C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=[CH:23][CH:22]=3)=O)CC=2C=1.ClC1C([N+:39]([O-:41])=[O:40])=CC=C(C)N=1.[C:43]1(B(O)O)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.C(Cl)Cl>[C:25]1([C:24]2[CH:23]=[CH:22][C:21]([N+:39]([O-:41])=[O:40])=[C:19]([CH3:43])[N:9]=2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 12682302-Chloro-6-methyl-3-nitropyridineHCID 1784796677-Bromo-2,3,4,5-tetrahydro-1-(1H-imidazol-4-ylmethyl)-4-(1-naphthalenylcarbonyl)-1H-1,4-benzodiazepine, hydrochloride

Product 1

HCID 149329632-Methyl-3-nitro-6-phenylpyridine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of Compound B and 2-chloro-3-nitro-6-methylpyridine (0.42 g, 2.40 mmol) in THF (10 mL) was degassed with nitrogen. Tetrakistriphenylphosphine palladium (28 mg, 0.024 mmol) was added and the mixture was stirred 30 minutes. 25 Phenylboronic acid (0.44 g, 3.6 mmol) and 2M Na2CO3 (1.8 mL) were added and the mixture was heated at 75° C. for 17 hours and stirred at room temperature for 48 hours. Methylene chloride was added and the mixture was filtered through celite and partitioned. The mixture was washed with saturated aqueous NaHCO3, dried (magnesium sulfate), filtered and evaporated to afford 0.77 g of brown solid. Flash chromatography (silica, 10% ethyl acetate/hexanes) afforded 0.37 g of Compound C (72%) as an off white solid and 0.05 g of 2-phenyl-3-nitro-6-methylpyridine (10%) as an oil.

Workup

  1. customwas degassed with nitrogen
  2. stirringstirred at room temperature for 48 hours
  3. filtrationthe mixture was filtered through celite
  4. custompartitioned
  5. washThe mixture was washed with saturated aqueous NaHCO3
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-a32d5c738da44ee385a620da10b56492
Source dataset
uspto-grants-2000_01
Patent number
US06011029

Reaction notes

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