Triethylamine → 4-Bromo-2-(3-(4-methoxyphenyl)-2H-azirin-2-yl)pyridine

HRID 1475930Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8]/[C:9](/[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[N:10]/O)[CH:3]=1.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[Cl-].[NH4+]>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]2[C:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)=[N:10]2)[CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of (Z)-2-(4-bromopyridin-2-yl)-1-(4-methoxyphenyl)ethanone oxime (2.7 g, 8.4 mmol) and triethylamine (4.7 mL, 33.6 mmol) in dichloromethane at 0° C., was added trifluoroacetic anhydride (1.3 mL, 9.2 mmol). The mixture was stirred at 0° C. for 20 minutes then at room temperature for 5 hours. A saturated solution of ammonium chloride (20 mL) was added and the mixture was diluted with dichloromethane (20 mL). The separated aqueous layer was extracted with dichloromethane (3×25 mL). The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to afford a residue which was purified by automated flash-chromatography (ethyl acetate/hexanes; 5/95). The title compound was obtained as a colorless solid (2.1 g, 83%); LCMS m/z 303.0, 305.0 (M+H)+, ret. time 2.57 min.

Workup

waitat room temperature for 5 hours
extractionThe separated aqueous layer was extracted with dichloromethane (3×25 mL)
washThe combined organic layers were washed with brine
dry with materialdried over anhydrous MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customto afford a residue which
customwas purified by automated flash-chromatography (ethyl acetate/hexanes; 5/95)

Sources & evidence

ORD record: ord-afeeab1b91b24a66a4625f0a74b682f5
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018395B2

Reaction notes

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