2-Chloro-5-nitropyridine → HCID 86690160, compound

HRID 1500211Notes

Reaction equation

HRID 1500211 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH:11]([C:13]1[C:14]([O:23][CH:24]([CH3:26])[CH3:25])=[C:15](B(O)O)[CH:16]=[C:17]([CH3:19])[CH:18]=1)=[O:12]>COCCOC>[CH:24]([O:23][C:14]1[C:15]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)=[CH:16][C:17]([CH3:19])=[CH:18][C:13]=1[CH:11]=[O:12])([CH3:26])[CH3:25]

Participants

4

Reactant 2

HCID 783082-Chloro-5-nitropyridineHCID 16217234{3-Formyl-5-methyl-2-[(propan-2-yl)oxy]phenyl}boronic acid

Product 1

HCID 86690160HCID 86690160, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

2-Chloro-5-nitropyridine (0.28 g, 1.76 mmol), 3-formyl-2-isopropoxy-5-methylphenylboronic acid (0.78 g, 3.52 mmol) and bis(di-tert-butyl(4-dimethylaminophenylphosphine)dichloropalladium(II) (0.012 g, 0.02 mmol) were added to 1,2-dimethoxyethan (9 ml), degassed and purged with nitrogen three times under reduced pressure. Under nitrogen atmosphere the mixture was stirred at room temperature for 30 minutes, 1M aqueous sodium carbonate (9 ml) was poured in, and the temperature was raised to 80° C. After the reaction at 80° C. for 23 hours, the mixture was cooled to room temperature and crystallized with addition of water. The crystallized crystals were filtered to give the title compound (0.49 g, 92.5%).

Workup

  1. customdegassed
  2. custompurged with nitrogen three times under reduced pressure
  3. addition1M aqueous sodium carbonate (9 ml) was poured in, and the temperature
  4. temperaturewas raised to 80° C
  5. customAfter the reaction at 80° C. for 23 hours
  6. temperaturethe mixture was cooled to room temperature
  7. customcrystallized with addition of water
  8. filtrationThe crystallized crystals were filtered

Sources & evidence

ORD record
ord-517098175ffe4cf0a9a2aea279455c8a
Source dataset
uspto-grants-2015_12
Patent number
US09206129B2

Reaction notes

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