Pyridine → N-(2-Bromo-6-fluorophenyl)pivalamide

HRID 1172359Notes

Reaction equation

HRID 1172359 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:3]=1[NH2:4].N1C=CC=CC=1.[C:16](Cl)(=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18]>>[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:3]=1[NH:4][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18]

Participants

4

Reactant 3

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 27829402-Bromo-6-fluoroaniline

Product 1

HCID 44203089N-(2-Bromo-6-fluorophenyl)pivalamideYield 76%

Procedure

2-Bromo-6-fluoroaniline (43.2 mmol, 8.2 g) was dissolved in pyridine (124 mmol, 10 mL). Pivaloyl chloride (57.15 mmol, 7.0 mL) was added to the mixture. Reaction was stirred at room temperature for 3 hours. Reaction mixture was concentrated in vacuo. Residue was treated with ethyl acetate (50 mL). Mixture was washed 2×1N HCl, 1× brine. Organic layer was dried (magnesium sulfate), filtered and concentrated in vacuo. Residue was treated with hexanes and triturated. Resulting solids were filtered off, washed with hexanes then dried in vacuo. Title compound was obtained as white solid in 76% yield. 1H NMR (300 MHz, CDCl3): δ=7.39-7.31 (m, 1H), 7.14-7.03 (m, 2H), 6.98 (bs, 1H), 1.34 (s, 9H). MS m/e (M+H)+=274.1, 276.1.

Workup

  1. customReaction
  2. customReaction mixture
  3. concentrationwas concentrated in vacuo
  4. additionResidue was treated with ethyl acetate (50 mL)
  5. washMixture was washed 2×1N HCl, 1× brine
  6. dry with materialOrganic layer was dried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. additionResidue was treated with hexanes
  10. customtriturated
  11. customResulting solids
  12. filtrationwere filtered off
  13. washwashed with hexanes
  14. customthen dried in vacuo

Sources & evidence

ORD record
ord-bcb7399423cf4f0394870dcfe7ea67ef
Source dataset
uspto-grants-2010_11
Patent number
US07834007B2

Reaction notes

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