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N-bromobutanimide → cis-4-[5-Bromo-6-(2-methyl-3-furanyl)-2-pyridinyl]-2,6-dimethylmorpholine

HRID 2278426
Notes
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Reaction equation

HRID 2278426 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]=[CH: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[CH: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]
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 67514523cis-2,6-Dimethyl-4-[6-(2-methyl-3-furanyl)-2-pyridinyl]morpholine

Product 1

HCID 86702424cis-4-[5-Bromo-6-(2-methyl-3-furanyl)-2-pyridinyl]-2,6-dimethylmorpholine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

N-Bromosuccinimide (137 mg, 0.771 mmol) was added portionwise to a solution of cis-2,6-dimethyl-4-[6-(2-methyl-3-furanyl)-2-pyridinyl]morpholine (210 mg, 0.771 mmol) in chloroform (7 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 (20 mL) and washed with water (10 mL), brine (10 mL), water (10 mL) and brine (10 mL). The organic layer was dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was dissolved in dichloromethane (˜10 ml) and purified on silica by a Biotage SP4 chromatographic system (40+S 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 as a colourless oil (280 mg, 0.678 mmol, 88% yield). LC/MS [M+H]+=351/353.

Sources & evidence

ORD record
ord-4e7f2f46809342f88c9e5fe92b2827e7
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09133178B2

Reaction notes

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On this pageParticipantsConditionsProcedureSources & evidenceReaction notes