N-bromobutanimide → HCID 127264019, compound
Reaction equation
C[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([O:10][CH3:11])[C:3]=1[CH3:12].[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:13][CH2:12][C:3]1[C:4]([O:10][CH3:11])=[N:5][CH:6]=[C:7]([CH:2]=1)[C:8]#[N:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of methyl 5-cyano-2-methoxy-3-methyl-pyridine (36) (0.25 g, 1.7 mmol) in CCl4 (10 mL) was added N-bromosuccinimide (346 mg, 1.7 mmol) and 2′,2-azobisisobutyronitrile (13.0 mg, 0.085 mmol). The reaction mixture was stirred at 80° C. for 1 h. The reaction mixture was filtered and the filtrate was concentrated to afford 5-(bromomethyl)-6-methoxy nicotinonitrile (37) as a yellow solid; (180 mg, 46.9%).
Workup
- filtrationThe reaction mixture was filtered
- concentrationthe filtrate was concentrated
Sources & evidence
- ORD record
- ord-c63f37c1b4c7465786ac5abd637ff512
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09163020B2
Reaction notes
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