Pivaloyl chloride → N-(5-Bromo-pyridin-3-yl)-2,2-dimethyl-propionamide

HRID 1472162Notes

Reaction equation

HRID 1472162 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1.[C:9](Cl)(=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11]>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 8176813-Amino-5-bromopyridine

Product 1

HCID 24229189N-(5-Bromo-pyridin-3-yl)-2,2-dimethyl-propionamideYield 73.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-amino-5-bromo pyridine (XXV) (1.0 g, 5.78 mmol) in dry pyridine (10 mL) was added pivaloyl chloride (XXVIII) (769 mg, 6.38 mmol). The reaction mixture was stirred at room temperature for 3 h. The reaction was poured into an ice water/saturated aqueous NaHCO3 mixture and stirred for 30 min. The precipitate was filtered, washed with cold water and dried at room temperature to yield N-(5-bromopyridin-3-yl)pivalamide (XXIX) as an off-white solid (1.082 g, 4.22 mmol, 73.1% yield). 1H NMR (DMSO-d6, 500 MHz) δ ppm 1.23 (s, 9H), 8.37 (d, J=2 Hz, 1H), 8.39 (t, J=2 Hz, 1H), 8.80 (d, J=2 Hz, 1H), 9.58 (brs, 1H); ESIMS found C10H13BrN2O m/z 257.0 (M+H).

Workup

  1. stirringstirred for 30 min
  2. filtrationThe precipitate was filtered
  3. washwashed with cold water
  4. customdried at room temperature

Sources & evidence

ORD record
ord-55b3668c4f3a42b8aa24f79d55820109
Source dataset
uspto-grants-2015_04
Patent number
US09012472B2

Reaction notes

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