2,4-Difluorobenzoyl chloride → HCID 86671069, compound

HRID 1182947Notes

Reaction equation

HRID 1182947 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[Br:12][C:13]1[CH:14]=[C:15]([NH2:20])[C:16]([Cl:19])=[N:17][CH:18]=1>C(Cl)(Cl)Cl>[Br:12][C:13]1[CH:14]=[C:15]([NH:20][C:4](=[O:5])[C:3]2[CH:7]=[CH:8][C:9]([F:11])=[CH:10][C:2]=2[F:1])[C:16]([Cl:19])=[N:17][CH:18]=1

Participants

4

Reactant 2

HCID 5880812,4-Difluorobenzoyl chlorideHCID 218583543-Amino-5-bromo-2-chloropyridine

Product 1

HCID 86671069HCID 86671069, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2,4-difluorobenzoyl chloride (0.33 g, 1.591 mmol) in CHCl3 (15.9 ml) were slowly added TEA (0.443 ml, 3.18 mmol) and 5-bromo-2-chloropyridin-3-amine (0.337 g, 1.91 mmol) at 0° C. The reaction mixture was stirred for 5 hours at room temperature. The reaction mixture was quenched with saturated aq. NaHCO3, and extracted with DCM (2×50 mL). The combined organic layers were washed brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on SiO2 (Hex:EtOAc=30:1) to give N-(5-bromo-2-chloropyridin-3-yl)-2,4-difluorobenzamide (0.185 g, 34%) as a white solid. 1H-NMR (CDCl3, Varian 400 MHz) δ 6.93-7.26 (2H, m), 8.21-8.27 (2H, m), 9.08-9.12 (1H, m), 9.16-9.16 (1H, m).

Workup

  1. customat 0° C
  2. customThe reaction mixture was quenched with saturated aq. NaHCO3
  3. extractionextracted with DCM (2×50 mL)
  4. washThe combined organic layers were washed brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography on SiO2 (Hex:EtOAc=30:1)

Sources & evidence

ORD record
ord-b2fe4469975c4b62bc59f102fc7f8025
Source dataset
uspto-grants-2014_03
Patent number
US08664230B2

Reaction notes

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