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

HRID 2188891Notes

Reaction equation

HRID 2188891 reaction equation
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[Br:8][C:9]1[CH:10]=[CH:11][C:12]([NH2:15])=[N:13][CH:14]=1.O>C(Cl)Cl.CCN(CC)CC>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])=[N:13][CH:14]=1

Participants

6

Reactant 3

HCID 962WaterHCID 62493Pivaloyl chlorideHCID 706222-Amino-5-bromopyridine

Product 1

HCID 15461537N-(5-bromopyridin-2-yl)-2,2-dimethylpropanamideYield 87.2%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6344DichloromethaneSolvent

Procedure

Pivaloyl chloride (85 mL, 0.69 mol) was added to a solution of 5-bromopyridin-2-amine (100 g, 0.58 mol) and Et3N (120 mL, 0.87 mmol.) in CH2Cl2 at −78° C. The temperature was allowed to warm to room temperature and the stirring was continued overnight. The reaction mixture was poured into water, extracted with CH2Cl2, dried over MgSO4, evaporated in vacuo and purified by chromatography on silica gel (10% EtOAc in petroleum ether) to afford N-(5-bromopyridin-2-yl)pivalamide (130 g, 87% yield). 1H NMR (CDCl3, 400 MHz) δ 8.28 (d, J=2.0 Hz, 1H), 8.17 (d, J=9.2 Hz, 1H), 7.99 (br s, 1H), 7.77 (dd, J=9.2 and 2.0, 1H), 1.28 (s, 9H).

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialdried over MgSO4
  3. customevaporated in vacuo
  4. custompurified by chromatography on silica gel (10% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-951f525c631f4b338608cf4f8846faa0
Source dataset
uspto-grants-2012_12
Patent number
US08324207B2

Reaction notes

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