Triethylamine → N-(5-bromo-2-chloropyridin-3-yl)-2-nitrobenzamide

HRID 44243

Reaction equation

HRID 44243 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([Cl:8])=[N:6][CH:7]=1.C(N(CC)CC)C.[N+:17]([C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1[C:22](Cl)=[O:23])([O-:19])=[O:18]>O1CCCC1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[Br:1][C:2]1[CH:3]=[C:4]([NH:9][C:22](=[O:23])[C:21]2[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=2[N+:17]([O-:19])=[O:18])[C:5]([Cl:8])=[N:6][CH:7]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 118752-Nitrobenzoyl chlorideHCID 218583543-Amino-5-bromo-2-chloropyridine

Product 1

HCID 86658034N-(5-bromo-2-chloropyridin-3-yl)-2-nitrobenzamide

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 5-bromo-2-chloropyridine-3-amine (3.9 g, 18.9 mmol) and triethylamine (5.3 mL, 37.9 mmol) in tetrahydrofuran (60 mL) was added 2-nitrobenzoylchloride (2.49 mL, 18.9 mmol). The reaction was stirred for 24 hours. The reaction mixture was diluted with ethyl acetate (200 mL) and saturated aqueous sodium bicarbonate (60 mL). The organic layer was separated and washed with water (50 mL), brine (50 mL), dried over sodium sulfate, filtered and concentrated to dryness under reduced pressure. The crude product was purified by flash chromatography (SiO2, 25% ethyl acetate in hexanes). The N-(5-bromo-2-chloropyridin-3-yl)-2-nitrobenzamide was obtained as a yellow solid (1.5 g). LCMS [M+H]: 356.

Workup

  1. customThe organic layer was separated
  2. washwashed with water (50 mL), brine (50 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe crude product was purified by flash chromatography (SiO2, 25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-ab89fc2dc2b24ffea8f46cdcfcbc29fa
Source dataset
uspto-grants-2013_09
Patent number
US08541407B2

Linked notes

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