N-bromobutanimide → cis-4-[5-Bromo-4-(2-methyl-3-furanyl)-2-pyridinyl]-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]=[C:21]([C:23]3[CH:27]=[CH:26][O:25][C:24]=3[CH3:28])[CH:20]=[CH:19][N:18]=2)[CH2:11]1>C(Cl)(Cl)Cl>[Br:1][C:20]1[C:21]([C:23]2[CH:27]=[CH:26][O:25][C:24]=2[CH3:28])=[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][CH:19]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
N-Bromosuccinimide (133 mg, 0.749 mmol) was added portionwise to a solution of cis-2,6-dimethyl-4-[4-(2-methyl-3-furanyl)-2-pyridinyl]morpholine (204 mg, 0.749 mmol) in chloroform (6 mL) at 0° C. The reaction was stirred at 0° C. for 1 hour. Crude LC/MS showed desired product can be seen and no starting material left, so the reaction mixture was diluted with ethyl acetate and washed with water, brine, water and brine. 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 (25+M cartridge, eluted with 0-50% ethyl acetate in isohexanes). Fractions containing pure product were combined and concentrated under reduced pressure to give the title compound (295 mg, 0.798 mmol, 107% yield) as a colourless oil. LC/MS [M+H]+=351/353.
Sources & evidence
- ORD record
- ord-1c5dd2f55e3346bf8e1e6802b91fff3c
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09133178B2
Reaction notes
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