Benzoyl chloride → N-(5-bromopyridin-3-yl)benzamide

HRID 1485525Notes

Reaction equation

HRID 1485525 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1.[C:9](Cl)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 8176813-Amino-5-bromopyridine

Product 1

HCID 66701388N-(5-bromopyridin-3-yl)benzamideYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromopyridin-3-amine (0.3 g, 1.734 mmol) in THF (8.67 ml) was added TEA (0.363 ml, 2.60 mmol), and then benzoyl chloride (0.292 g, 2.081 mmol) was added to the mixture at 0° C. After stirred for 2 hours at room temperature, the reaction mixture was quenched with saturated aq. NaHCO3 (50 mL) and extracted with EtOAc (2×50 mL). The combined organic layers were washed with water and brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on SiO2 (Hex:EtOAc=10:1) to give N-(5-bromopyridin-3-yl)benzamide (0.435 g, 91%) as a yellow solid. 1H-NMR (CDCl3, Varian 400 MHz) δ 7.48 (2H, t, J=7.6 Hz), 7.58 (1H, t, J=7.4 Hz), 7.85-7.88 (2H, m), 8.38 (1H, brs), 8.40 (1H, d, J=1.6 Hz), 8.56-8.58 (2H, m).

Workup

  1. customthe reaction mixture was quenched with saturated aq. NaHCO3 (50 mL)
  2. extractionextracted with EtOAc (2×50 mL)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on SiO2 (Hex:EtOAc=10:1)

Sources & evidence

ORD record
ord-b0d89444f75b4c0a9f2a1443ec659599
Source dataset
uspto-grants-2016_08
Patent number
US09422298B2

Reaction notes

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