N-bromobutanimide → Ethyl 6-oxo-2-(pentafluoroethyl)-1,6-dihydropyridine-3-carboxylate

HRID 2421030

Reaction equation

[O:1]=[C:2]1[NH:7][C:6]([C:8]([F:14])([F:13])[C:9]([F:12])([F:11])[F:10])=[C:5]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:4][CH2:3]1.BrN1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[O:1]=[C:2]1[NH:7][C:6]([C:8]([F:13])([F:14])[C:9]([F:10])([F:11])[F:12])=[C:5]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:4]=[CH:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of ethyl 6-oxo-2-(pentafluoroethyl)-1,4,5,6-tetrahydropyridine-3-carboxylate (0.690 g) and N-bromosuccinimide (0.427 g) in carbon tetrachloride (5 mL) was heated at 80° C. for 20 h. The reaction mixture was concentrated in vacuo and subjected to flash column chromatography (eluent 1:3 ethyl acetate/isohexane) to yield a colourless solid (0.30 g).

Workup

concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record: ord-885a408ad58b46549dc94731e4f37375
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07956070B2

Linked notes

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