N-bromobutanimide → Methyl 3-amino-6-bromo-5-fluoropicolinate

HRID 1499433Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1499433
[NH2:1][C:2]1[C:3]([C:9]([O:11][CH3:12])=[O:10])=[N:4][CH:5]=[C:6]([F:8])[CH:7]=1.[Br:13]N1C(=O)CCC1=O>CC#N.CCOC(C)=O>[NH2:1][C:2]1[C:3]([C:9]([O:11][CH3:12])=[O:10])=[N:4][C:5]([Br:13])=[C:6]([F:8])[CH:7]=1

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 66652559Methyl 3-amino-5-fluoropicolinate

Produkt 1

HCID 72698878Methyl 3-amino-6-bromo-5-fluoropicolinateAusbeute 76,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of methyl 3-amino-5-fluoropyridine-2-carboxylate (3.6 g, 21 mmol) in MeCN (60 mL), N-bromosuccinimide (4.1 g, 23 mmol) was added portionwise. After stirring at room temperature for 2 h, the reaction mixture was diluted with EtOAc (200 mL), washed with a saturated aq. NaHCO3 (200 mL) and brine (200 mL), then dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was purified by chromatography on silica gel (0-100% EtOAc in hexanes) to afford the sub-title compound as a pale yellow solid (4.0 g, 76%) LCMS calc. for C7H7BrFN2O2 (M+H)+: m/z=249.0. found 249.0.

Aufarbeitung

  1. washwashed with a saturated aq. NaHCO3 (200 mL) and brine (200 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by chromatography on silica gel (0-100% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-c3cb830fcd024878afe2dfb899ab2a44
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09200004B2

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