Di-tert-butyl dicarbonate → HCID 59603463, Verbindung

HRID 272764Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 272764
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1.[O:11](C(OC(C)(C)C)=O)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=O>CN(C1C=CN=CC=1)C.O1CCOCC1>[C:15]([O:14][C:12]([N:4]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:10]2[C:2]([Br:1])=[CH:3]1)=[O:11])([CH3:18])([CH3:17])[CH3:16]

Komponenten

5

Edukt 2

HCID 90495Di-tert-butyl dicarbonateHCID 124108563-Bromo-1H-pyrrolo[2,3-c]pyridine

Produkt 1

HCID 59603463HCID 59603463, VerbindungAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of Example 695J (0.32 g, 1.62 mmol), (BOC)2O (0.43 g, 1.94 mmol) and DMAP (50 mg) in 10 mL of dioxane was stirred overnight at room temperature. The reaction mixture was partitioned between water and EtOAc. The aqueous layer was extracted with additional EtOAc. The combined organic layers were washed with water, brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with 7:3 hexanes/ethyl acetate to provide 0.36 g (75%) of the desired product. MS (APCI) m/e 298 (M+H)+, 1H NMR (500 MHz, DMSO-d6): □ 9.29 (s, 1H), 8.28 (d, J=5.09 Hz, 1H), 8.16 (s, 1H), 7.55 (d, J=5.43 Hz, 1H), 1.65 (s, 9H).

Aufarbeitung

  1. customThe reaction mixture was partitioned between water and EtOAc
  2. extractionThe aqueous layer was extracted with additional EtOAc
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography on silica gel eluting with 7:3 hexanes/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-8d1eef322d3940659cd9060b39be7eb8
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456169B2

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