Bromine → 4-(3-bromoimidazo[1,2-a]pyrimidin-6-yl)-2-fluoro-N-methylbenzamide

HRID 500128Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 500128
[Br:1]Br.C([O-])(=O)C.[Na+].[F:8][C:9]1[CH:18]=[C:17]([C:19]2[CH:20]=[N:21][C:22]3[N:23]([CH:25]=[CH:26][N:27]=3)[CH:24]=2)[CH:16]=[CH:15][C:10]=1[C:11]([NH:13][CH3:14])=[O:12]>C(O)(=O)C>[Br:1][C:25]1[N:23]2[CH:24]=[C:19]([C:17]3[CH:16]=[CH:15][C:10]([C:11]([NH:13][CH3:14])=[O:12])=[C:9]([F:8])[CH:18]=3)[CH:20]=[N:21][C:22]2=[N:27][CH:26]=1

Komponenten

5

Edukt 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 672248512-fluoro-4-imidazo[1,2-a]pyrimidin-6-yl-N-methylbenzamide

Produkt 1

HCID 672244434-(3-bromoimidazo[1,2-a]pyrimidin-6-yl)-2-fluoro-N-methylbenzamideAusbeute 88,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Bromine (17.4 μL, 0.338 mmol) was added to a mixture of sodium acetate (40.3 mg, 0.491 mmol) and 2-fluoro-4-imidazo[1,2-a]pyrimidin-6-yl-N-methylbenzamide (83.0 mg, 0.307 mmol) in acetic acid (2.6 mL) and the reaction mixture was stirred at ambient temperature for 30 min. The solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate and washed with saturated sodium bicarbonate and brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by chromatography on silica gel with ethyl acetate in dichloromethane (0-50%) to afford the desired product (95 mg, 88.6%). LCMS: (M+H)=348.8/350.9.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with saturated sodium bicarbonate and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel with ethyl acetate in dichloromethane (0-50%)

Quellen und Nachweise

ORD-Eintrag
ord-c110ce9ad52c4882af563dd2613305ce
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07767675B2

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