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

HRID 869872Notes

Reaction equation

HRID 869872 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.CCN(CC)CC.O>C(Cl)Cl>[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 4

HCID 962WaterHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 706222-Amino-5-bromopyridine

Product 1

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

Reagents, catalysts & solvents 1

HCID 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 silica gel column chromatography (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 silica gel column chromatography (10% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-aee3714802ec4f58a58138b4be5ed8ff
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

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