N-bromobutanimide → (S)-6-bromo-5-cyclobutoxy-7,8-difluoro-2-methyl-1,2,3,4-tetrahydroquinoline
Reaction equation
[Br:1]N1C(=O)CCC1=O.[CH:9]1([O:13][C:14]2[CH:23]=[C:22]([F:24])[C:21]([F:25])=[C:20]3[C:15]=2[CH2:16][CH2:17][C@H:18]([CH3:26])[NH:19]3)[CH2:12][CH2:11][CH2:10]1>C(#N)C.ClCCl>[Br:1][C:23]1[C:14]([O:13][CH:9]2[CH2:10][CH2:11][CH2:12]2)=[C:15]2[C:20](=[C:21]([F:25])[C:22]=1[F:24])[NH:19][C@@H:18]([CH3:26])[CH2:17][CH2:16]2Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -5 °C
Procedure
A solution of N-bromosuccinimide (0.703 g, 3.95 mmol) in acetonitrile (10 mL) was added dropwise to a −5° C. solution of (S)-5-cyclobutoxy-7,8-difluoro-2-methyl-1,2,3,4-tetrahydroquinoline (1.0 g, 3.95 mmol) in acetonitrile (80 mL) and dichloromethane (15 mL), and the resulting solution stirred for 4 h at −5° C. The reaction mixture was concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with 50% ethyl acetate/petroleum ether) to afford (S)-6-bromo-5-cyclobutoxy-7,8-difluoro-2-methyl-1,2,3,4-tetrahydroquinoline (1.05 g, 81%) as a yellow solid. MS (ESI, pos. ion) m/z 332, 334 [M+H]+.
Workup
- concentrationThe reaction mixture was concentrated under vacuum
- customThe residue was purified via column chromatography on silica gel (eluting with 50% ethyl acetate/petroleum ether)
Sources & evidence
- ORD record
- ord-9d4bf9fdfea04044bf1f391632fc6d9b
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09388161B2
Reaction notes
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