Pivaloyl chloride → N-(5-bromopyridin-2-yl)-2,2-dimethylpropanamide

HRID 611617Notes

Reaction equation

HRID 611617 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[C:3](Cl)=[O:4].[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][N:10]=1>ClCCl.C(N(CC)CC)C>[Br:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:3](=[O:4])[C:2]([CH3:7])([CH3:6])[CH3:1])=[N:10][CH:11]=1

Participants

5

Reactant 2

HCID 62493Pivaloyl chlorideHCID 706222-Amino-5-bromopyridine

Product 1

HCID 15461537N-(5-bromopyridin-2-yl)-2,2-dimethylpropanamideYield 70%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
20 °C

Procedure

A solution of trimethylacetyl chloride (17.5 g, 146 mmol) in dichloromethane (25 ml) was added to a solution of 2-amino-5-bromopyridine (25.0 g, 144 mmol) in dichloromethane (100 ml) and triethylamine (24 ml) dropwise with stirring at 20° C. The reaction mixture was then stirred for 40 minutes, filtered, washed with water, dried and concentrated. Recrystallization from hexanes afforded 20.6 g (70%) of the title product as a white flaky solid. mp 63-64° C. 1H NMR (CDCl3): δ=8.82 (br, 1 H); 8.30 (d, 1 H); 8.19 (m, 2 H); 1.36 (s, 3 H). MS (El): m/z=256, 258 (M+, Br isotopes).

Workup

  1. stirringThe reaction mixture was then stirred for 40 minutes
  2. filtrationfiltered
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated
  6. customRecrystallization from hexanes

Sources & evidence

ORD record
ord-4c768e06a5094f369d1a2c86c8af9d39
Source dataset
uspto-grants-1999_12
Patent number
US06001856

Reaction notes

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