Pyridine → N-(6-bromo-5-chloropyridin-2-yl)benzamide

HRID 1521938Notes

Reaction equation

HRID 1521938 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[Cl:9].N1C=CC=CC=1.[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>ClCCl>[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:5]=[CH:4][C:3]=1[Cl:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 534011936-Bromo-5-chloropyridin-2-amine

Product 1

HCID 90412314N-(6-bromo-5-chloropyridin-2-yl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 11A (400 mg, 1.928 mmol) in dichloromethane (20 mL) was added pyridine (0.468 mL, 5.78 mmol) followed by benzoyl chloride (0.325 g, 2.314 mmol) and the mixture was stirred for 2 hours. The mixture was concentrated and the residue was dissolved in ethyl acetate, washed with sodium bicarbonate solution, water and brine, and dried over anhydrous sodium sulfate. Filtration, concentration and purification by column chromatography (silica gel, 10% ethyl acetate in hexane) afforded the title compound. LCMS: 311 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with sodium bicarbonate solution, water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationFiltration, concentration and purification by column chromatography (silica gel, 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-17b5a27fd8c343f8ac24e8af0731ba07
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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