Pivaloyl chloride → N-(6-Bromopyridin-2-yl)-2,2-dimethylpropanamide

HRID 531441Notes

Reaction equation

HRID 531441 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.[C:9](Cl)(=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11].C(N(C(C)C)C(C)C)C>C(Cl)Cl.CCOCC>[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 62493Pivaloyl chlorideHCID 81531DiisopropylethylamineHCID 3008092-Amino-6-bromopyridine

Product 1

HCID 9921361N-(6-Bromopyridin-2-yl)-2,2-dimethylpropanamideYield 69.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To an ice cold solution of 6-bromopyridine-2-amine (7 g, 40.5 mmol) in DCM was added pivaloyl chloride (5.23 mL, 42.48 mmol), N-ethyl-N-isopropylpropan-2-amine (13.6 mL, 82.9 mmol) sequentially. The solution was stirred for an hour then diluted with 50 mL of ether. The mixture was washed with saturated sodium bicarbonate. The organic layer was dried over sodium sulfate, filtered concentrated. The residue was slowly solidified after scratching in ethyl acetate-hexane mixture to afford 7.2 gm (69.2% yield) of the titled compound. LCMS: m/z=257.0 (M+1).

Workup

  1. washThe mixture was washed with saturated sodium bicarbonate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8d648f88249541359d50e3a4dc9d7474
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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