Sodium Carbonate → 2-Amino-3-nitro-5-phenylpyridine

HRID 1644588Notes

Reaction equation

HRID 1644588 reaction equation
Br[C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([NH2:8])=[N:6][CH:7]=1.[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(COC)OC>[N+:9]([C:4]1[C:5]([NH2:8])=[N:6][CH:7]=[C:2]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:3]=1)([O-:11])=[O:10]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 1388782-Amino-5-bromo-3-nitropyridine

Product 1

HCID 108225552-Amino-3-nitro-5-phenylpyridineYield 46.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 5-bromo-3-nitropyridine-2-amine (10 g), phenylboronic acid (8.39 g), tetrakis(triphenylphosphine)palladium(0) (5.3 g), 2N aqueous sodium carbonate solution (100 ml) and dimethoxyethane (500 ml) was heated under reflux under an argon atmosphere for 5 hr. The insoluble material was removed by filtration, and the filtrate was concentrated, diluted with water and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and concentrated. The obtained crude crystals were washed with diethyl ether to give the title compound (4.58 g, yield 46%) as yellow crystals. purity 80%. M+H: 216.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux under an argon atmosphere for 5 hr
  3. customThe insoluble material was removed by filtration
  4. concentrationthe filtrate was concentrated
  5. additiondiluted with water
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed with water
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated
  10. customThe obtained crude crystals
  11. washwere washed with diethyl ether

Sources & evidence

ORD record
ord-298827bba1254eb3a3c5a4532e77f5c3
Source dataset
uspto-grants-2012_02
Patent number
US08124617B2

Reaction notes

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