N-bromobutanimide → 3-Bromo-8-(2,6-dichloro-3-nitrobenzyloxy)-2-methylimidazo[1,2-a]pyridine

HRID 1899986Notes

Reaction equation

HRID 1899986 reaction equation
[Cl:1][C:2]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][CH:17]=[C:16]([Cl:23])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([CH:12]=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1.[Br:24]N1C(=O)CCC1=O>C(O)C.O1CCOCC1>[Br:24][C:12]1[N:8]2[CH:9]=[CH:10][CH:11]=[C:6]([O:5][CH2:4][C:3]3[C:16]([Cl:23])=[CH:17][CH:18]=[C:19]([N+:20]([O-:22])=[O:21])[C:2]=3[Cl:1])[C:7]2=[N:14][C:13]=1[CH3:15]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 108078918-(2,6-Dichloro-3-nitrobenzyloxy)-2-methylimidazo[1,2-a]pyridine

Product 1

HCID 117969163-Bromo-8-(2,6-dichloro-3-nitrobenzyloxy)-2-methylimidazo[1,2-a]pyridineYield 81.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 8-(2,6-dichloro-3-nitrobenzyloxy)-2-methylimidazo[1,2-a]pyridine (85 mg) in a mixture of ethanol (1 ml) and 1,4-dioxane (1 ml) was added in one portion N-bromosuccinimide (43 mg) at ambient temperature. After stirring for one hour at the same temperature, the mixture was filtered to give 3-bromo-8-(2,6-dichloro-3-nitrobenzyloxy)-2-methylimidazo[1,2-a]pyridine (85 mg) as a yellow solid.

Workup

  1. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-ad272ca026ac4bd49a16723cf5ae9e9d
Source dataset
uspto-grants-1996_11
Patent number
US05574042

Reaction notes

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