2-amino-5-bromo-N-methoxy-N-methylnicotinamide → 2-Amino-3-(2-methoxybenzoyl)-5-bromopyridine

HRID 603083

Reaktionsgleichung

Reaktionsgleichung von HRID 603083
[NH2:1][C:2]1[N:13]=[CH:12][C:11]([Br:14])=[CH:10][C:3]=1[C:4](N(OC)C)=[O:5].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[Mg]Br>C1COCC1>[NH2:1][C:2]1[C:3]([C:4]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[O:16][CH3:15])=[O:5])=[CH:10][C:11]([Br:14])=[CH:12][N:13]=1

Komponenten

4

Edukt 2

HCID 596997242-amino-5-bromo-N-methoxy-N-methylnicotinamideHCID 178489560HCID 178489560, Verbindung

Produkt 1

HCID 451083192-Amino-3-(2-methoxybenzoyl)-5-bromopyridineAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-55 °C

Versuchsvorschrift

To a flame-dried 100 ml round bottomed flask were added 2-amino-5-bromo-N-methoxy-N-methyl-nicotinamide (661 mg, 2.54 mmol) and anhydrous THF (15 ml). The solution was stirred at −55° C. for 5 minutes under nitrogen, then a 0.5 M solution of 2-methoxyphenyl magnesium bromide in THF (18 ml, 9.0 mmol) was added dropwise over 3 minutes. The resulting solution was allowed to warm to room temperature over 2 hours then quenched by addition of 1 M citric acid (25 ml). Ethyl acetate (50 ml) was added, and the layers were separated. The aqueous fraction was extracted three times with ethyl acetate, and the combined organic fractions were washed with brine, dried (Na2SO4), filtered and concentrated to give a sticky yellow solid. Recrystallization from ethanol provided 619.5 mg (79%) of (2-amino-5-bromo-pyridin-3-yl)-(2-methoxy-phenyl)-methanone as yellow needles. MS m/z: 308 [MH]+.

Aufarbeitung

  1. temperatureto warm to room temperature over 2 hours
  2. customthen quenched by addition of 1 M citric acid (25 ml)
  3. additionEthyl acetate (50 ml) was added
  4. customthe layers were separated
  5. extractionThe aqueous fraction was extracted three times with ethyl acetate
  6. washthe combined organic fractions were washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give a sticky yellow solid
  11. customRecrystallization from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-6c19c9453b8047419fdb7e71f4503476
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906648B2

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