Trimethylsilyldiazomethane → Methyl 6-amino-3-bromopyridine-2-carboxylate

HRID 1430294Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1430294
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[C:5]([Br:11])=[CH:4][CH:3]=1.[Si](C=[N+]=[N-])(C)(C)[CH3:13]>C(OCC)(=O)C.CO>[NH2:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:13])=[O:9])[C:5]([Br:11])=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 167693TrimethylsilyldiazomethaneHCID 467388136-Amino-3-bromopyridine-2-carboxylic acid

Produkt 1

HCID 10657127Methyl 6-amino-3-bromopyridine-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 6-amino-3-bromopicolinic acid (30 g) in ethyl acetate (300 mL) and methanol (300 mL) was added TMS-diazomethane (70 mL, 2M in hexanes) and the reaction mixture was stirred for 3 days. The mixture was concentrated, taken up in ether (500 mL) and washed with aqueous saturated Na2CO3 solution (twice) and brine, then dried over sodium sulfate, filtered and concentrated to provide the title compound.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. washwashed with aqueous saturated Na2CO3 solution (twice) and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-cf677f89497042ea8bac91e072269dce
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08940737B2

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