N-Bromosuccinamide → 2-Bromo-N,N-dipropylimidazo[1,2-a]pyridin-5-amine

HRID 2235540Notes

Reaction equation

HRID 2235540 reaction equation
[CH2:1]([N:4]([CH2:14][CH2:15][CH3:16])[C:5]1[N:10]2[CH:11]=[CH:12][N:13]=[C:9]2[CH:8]=[CH:7][CH:6]=1)[CH2:2][CH3:3].[Br:17]NC(=O)CCC(N)=O>CN(C=O)C>[Br:17][C:12]1[N:13]=[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:14][CH2:15][CH3:16])[N:10]2[CH:11]=1

Participants

4

Reactant 2

HCID 9834204N-BromosuccinamideHCID 68581368HCID 68581368, compound

Product 1

HCID 685819902-Bromo-N,N-dipropylimidazo[1,2-a]pyridin-5-amineYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

N,N-Dipropylimidazo[1,2-a]pyridin-5-amine (1.0 g, 4.6 mmol) was diluted in DMF (25 mL). The solution was cooled to 0° C. N-bromosuccinamide (0.83 g, 4.7 mmol) was added. After 5 minutes, the reaction was quenched with water. The solution was extracted with ether, dried, and concentrated. Flash chromatography (40% EtOAc/hexanes) gave the title compound as a yellow oil which solidified upon overnight freezing at −20° C. 0.67 g obtained (49% yield).

Workup

  1. customthe reaction was quenched with water
  2. extractionThe solution was extracted with ether
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7e629ca5076c4bcc8ebce8796c5d40c8
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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