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

HRID 2420866Notes

Reaction equation

HRID 2420866 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-b4dafd4d7ea645b1ac9a46e538faf16b
Source dataset
uspto-grants-2011_06
Patent number
US07956052B2

Reaction notes

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