2-Chloro-3-nitropyridine → HCID 58577470, compound

HRID 587426Notes

Reaction equation

HRID 587426 reaction equation
[N:1]1([C:13]2[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=2)[C:5]2=[N:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:4]2[CH2:3][CH2:2]1.Cl[C:21]1[C:26]([N+:27]([O-:29])=[O:28])=[CH:25][CH:24]=[CH:23][N:22]=1>CN1C(=O)CCC1.O>[N:1]1([C:13]2[CH:19]=[CH:18][C:16]([NH:17][C:21]3[C:26]([N+:27]([O-:29])=[O:28])=[CH:25][CH:24]=[CH:23][N:22]=3)=[CH:15][CH:14]=2)[C:5]2=[N:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:4]2[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 796132-Chloro-3-nitropyridineHCID 58577267HCID 58577267, compound

Product 1

HCID 58577470HCID 58577470, compoundYield 41.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 4-(2,3-dihydro-1H-imidazo[1,2-a]benzimidazol-1-yl)aniline (55 mg) and 2-chloro-3-nitropyridine (35 mg) in NMP (3 mL) was stirred at 140° C. overnight. After this time, the reaction mixture was cooled to ambient temperature, diluted with water (50 mL) and extracted with ethyl acetate (2×75 mL). The combined organic layers were washed with water (50 mL) then brine (50 mL), dried over sodium sulfate, and filtered and the filtrate was concentrated under reduced pressure. The residue obtained was purified by chromatography (silica, methylene chloride to 1:9 ethyl acetate/methylene chloride) to afford N-[4-(2,3-dihydro-1H-imidazo[1,2-a]benzimidazol-1-yl)phenyl]-3-nitropyridin-2-amine (34 mg) as a dark brown solid.

Workup

  1. temperatureAfter this time, the reaction mixture was cooled to ambient temperature
  2. extractionextracted with ethyl acetate (2×75 mL)
  3. washThe combined organic layers were washed with water (50 mL)
  4. dry with materialbrine (50 mL), dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue obtained
  8. customwas purified by chromatography (silica, methylene chloride to 1:9 ethyl acetate/methylene chloride)

Sources & evidence

ORD record
ord-1af18980c6984ff6b95e08da0e0206e1
Source dataset
uspto-grants-2016_01
Patent number
US09226921B2

Reaction notes

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