Pyridine → HCID 10817049, compound
Reaction equation
[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][CH2:12][C:13]3[C:18]([Cl:19])=[CH:17][CH:16]=[C:15]([NH:20][CH3:21])[C:14]=3[Cl:22])[C:5]2=[N:4][C:3]=1[CH3:23].N1C=CC=CC=1.Cl[C:31]([O:33][C:34]1[CH:39]=[CH:38][C:37]([N+:40]([O-:42])=[O:41])=[CH:36][CH:35]=1)=[O:32]>ClCCl>[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][CH2:12][C:13]3[C:18]([Cl:19])=[CH:17][CH:16]=[C:15]([N:20]([CH3:21])[C:31]([O:33][C:34]4[CH:39]=[CH:38][C:37]([N+:40]([O-:42])=[O:41])=[CH:36][CH:35]=4)=[O:32])[C:14]=3[Cl:22])[C:5]2=[N:4][C:3]=1[CH3:23]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3-bromo-8-(2,6-dichloro-3-methylaminobenzyloxy)-2-methylimidazo[1,2-a]-pyridine (68 mg) and pyridine (0.5 ml) in dichloromethane (2 ml) was added 4-nitrophenyl chloroformate (40 mg) at ambient temperature. After stirring for 1 hour, the mixture was partitioned between dichloromethane and water. The aqueous layer was extracted with dichloromethane twice. The organic layers were combined, washed with water twice and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was crystallized from diethyl ether to give 3-bromo-8-[2,6-dichloro-3-[N-methyl-N-(4-nitrophenoxycarbonyl)amino]benzyloxy]-2-methylimidazo[1,2-a]pyridine (84 mg) as crystals.
Workup
- customthe mixture was partitioned between dichloromethane and water
- extractionThe aqueous layer was extracted with dichloromethane twice
- washwashed with water twice
- dry with materialbrine, dried over magnesium sulfate
- customevaporated in vacuo
- customThe residue was crystallized from diethyl ether
Sources & evidence
- ORD record
- ord-104e6b8a61844841b29e1ea736dbc2ed
- Source dataset
- uspto-grants-1998_05
- Patent number
- US05750699
Reaction notes
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