Sodium Carbonate → HCID 13546598, compound

HRID 249694Notes

Reaction equation

HRID 249694 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4](Cl)[N:3]=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Li+]>ClCCl.O.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(O)C.C1(C)C=CC=CC=1.O>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:4]2[N:3]=[C:2]([NH2:1])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=2)=[CH:15][CH:14]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 433294Lithium ChlorideHCID 27240356-Chloro-3-nitropyridin-2-ylamine

Product 1

HCID 13546598HCID 13546598, compoundYield 27.5%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 86587398Ethanol toluene waterSolvent

Conditions

Temperature
90 °C

Procedure

Under a nitrogen atmosphere, 1 g (5.76 mmol) of 2-amino-6-chloro-3-nitropyridine is mixed with 1.26 g (8.07 mmol) of 4-chlorobenzeneboronic acid, 7.2 ml (14.4 mmol) of a 2M aqueous solution of sodium carbonate and 0.7 g (16.36 mmol) of lithium chloride in 44 ml of a pre-degassed mixture of ethanol/toluene/water (v/v: 1/1/0.4). 0.34 g (0.29 mmol) of tetrakis(triphenylphosphine)palladium(0) is added. The mixture is heated at 90° C. with stirring for 18 hours. The resulting mixture is cooled to ambient temperature and then diluted with 50 ml of dichloromethane and 25 ml of water. The organic phase is separated by settling out and washed with 25 ml of water and 25 ml of a saturated solution of sodium chloride. The resulting product is dried over sodium sulfate and evaporated to dryness. The product is purified by silica gel chromatography, elution being carried out with a 50:50 then 80:20 mixture of dichloromethane and cyclohexane. 0.395 g (yield: 27%) of 6-(4-chlorophenyl)-3-nitropyridin-2-ylamine is obtained in the form of a white powder.

Workup

  1. temperatureThe resulting mixture is cooled to ambient temperature
  2. customThe organic phase is separated
  3. washwashed with 25 ml of water and 25 ml of a saturated solution of sodium chloride
  4. dry with materialThe resulting product is dried over sodium sulfate
  5. customevaporated to dryness
  6. customThe product is purified by silica gel chromatography, elution
  7. addition80:20 mixture of dichloromethane and cyclohexane

Sources & evidence

ORD record
ord-8a6a478f853c4d8bae280c776b6ddf0a
Source dataset
uspto-grants-2011_01
Patent number
US07863279B2

Reaction notes

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