N-bromobutanimide → cis-4-[5-Bromo-6-(2-methyl-3-furanyl)-2-pyrazinyl]-2,6-dimethylmorpholine
Reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][C@H:10]1[O:15][C@@H:14]([CH3:16])[CH2:13][N:12]([C:17]2[CH:22]=[N:21][CH:20]=[C:19]([C:23]3[CH:27]=[CH:26][O:25][C:24]=3[CH3:28])[N:18]=2)[CH2:11]1>C(Cl)(Cl)Cl>[Br:1][C:20]1[N:21]=[CH:22][C:17]([N:12]2[CH2:11][C@H:10]([CH3:9])[O:15][C@H:14]([CH3:16])[CH2:13]2)=[N:18][C:19]=1[C:23]1[CH:27]=[CH:26][O:25][C:24]=1[CH3:28]Participants
Conditions
- Temperature
- 0 °C
Procedure
N-Bromosuccinimide (272 mg, 1.529 mmol) was added portionwise to a solution of cis-2,6-dimethyl-4-[6-(2-methyl-3-furanyl)-2-pyrazinyl]morpholine (418 mg, 1.529 mmol) in chloroform (13 mL) at 0° C. The reaction was stirred at 0° C. for 1 hour. Crude LC/MS shows desired product can be seen and no starting material left, so reaction mixture was diluted with ethyl acetate (20 mL) and washed with water (50 mL), brine (50 mL), water (50 mL) and brine (50 mL). The organic layer was dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was dissolved in dichloromethane (˜5 mL) and purified on silica by a Biotage SP4 chromatographic system (40+M cartridge, eluted with 0-100% ethyl acetate in isohexanes). Fractions containing pure product were combined and concentrated under reduced pressure to give the title compound (210 mg, 0.566 mmol, 37.0% yield). LC/MS [M+H]+=352/354.
Sources & evidence
- ORD record
- ord-062ac3f4aaa84a75b352710ece05240d
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09133178B2
Reaction notes
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