Triethylamine → N-(5-bromopyridin-2-yl)-2,2-dimethylpropanamide

HRID 378561Notes

Reaction equation

HRID 378561 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.C(N(CC)CC)C.[CH3:16][C:17]([CH3:22])([CH3:21])[C:18](Cl)=[O:19]>ClCCl>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:18](=[O:19])[C:17]([CH3:22])([CH3:21])[CH3:16])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 706222-Amino-5-bromopyridine

Product 1

HCID 15461537N-(5-bromopyridin-2-yl)-2,2-dimethylpropanamideYield 45.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5.00 g (28.9 mmol) of 2-amino-5-bromopyridine in 20 mL of dichloromethane was treated sequentially with 3.50 g (34.6 mmol) of triethylamine followed by 3.50 g (29.2 mmol) of trimethylacetyl chloride. The reaction mixture was filtered after about 1 hour, and the filtrate was evaporated to a colorless oil. This was crystallized from hexanes, filtered and washed to afford 3.36 g of N-(5-bromo-pyridin-2-yl)-2,2-dimethyl-propionamide as white crystals, mp 57-59° C. 1H NMR (deuterochloroform) δ=8.28 (d, 1 H); 8.16 (d, 1 H); 7.96 (br, 1 H); 7.75 (d of d, 1 H); 1.29 (s, 9 H): MS (NH3CL): m/z=257,259 (M+H+, Br isotopes).

Workup

  1. filtrationThe reaction mixture was filtered after about 1 hour
  2. customthe filtrate was evaporated to a colorless oil
  3. customThis was crystallized from hexanes
  4. filtrationfiltered
  5. washwashed

Sources & evidence

ORD record
ord-e58c82e544454463a349f27ea98d1719
Source dataset
uspto-grants-2000_02
Patent number
US06031105

Reaction notes

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