N-bromobutanimide → 6-Bromo-5-chloro-1,2,3,4-tetrahydro-1,8-naphthyridine
Reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][NH:7]2.[Br:12]N1C(=O)CCC1=O>C(Cl)Cl>[Br:12][C:11]1[C:2]([Cl:1])=[C:3]2[C:8](=[N:9][CH:10]=1)[NH:7][CH2:6][CH2:5][CH2:4]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 5-chloro-1,2,3,4-tetrahydro-[1,8]naphthyridine (500 mg, 3.0 mmol) in DCM (40 mL) is added N-bromosuccinimide (530 mg, 3.0 mmol). The reaction mixture is stirred at room temperature for 2 hrs. The reaction mixture is concentrated to give the crude product. Purification by flash column chromatography affords 680 mg of 6-bromo-5-chloro-1,2,3,4-tetrahydro-[1,8]naphthyridine.
Workup
- concentrationThe reaction mixture is concentrated
- customto give the crude product
- customPurification by flash column chromatography
Sources & evidence
- ORD record
- ord-518f038ee1934b28962cb8c8181f76ef
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181272B2
Reaction notes
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