N-bromobutanimide → 1-(1-bromo-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-chloro-2-phenylethanone

HRID 2383435Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2383435
[Cl:1][CH:2]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:3]([N:5]1[CH2:14][C:13]2[CH:12]=[N:11][C:10]3[NH:15][N:16]=[CH:17][C:9]=3[C:8]=2[CH2:7][CH2:6]1)=[O:4].[Br:24]N1C(=O)CCC1=O>ClCCl>[Br:24][C:17]1[C:9]2[C:8]3[CH2:7][CH2:6][N:5]([C:3](=[O:4])[CH:2]([Cl:1])[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH2:14][C:13]=3[CH:12]=[N:11][C:10]=2[NH:15][N:16]=1

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 594906052-chloro-1-(8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-phenylethanone

Produkt 1

HCID 1785207811-(1-bromo-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-chloro-2-phenylethanoneAusbeute 90,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-chloro-1-(8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-phenylethanone (0.340 g, 1.04 mmol) in dichloromethane (20 mL) was added N-bromosuccinimide (NBS, 0.195 g, 1.09 mmol). The reaction mixture was stirred for 16 hours at room temperature. During the reaction a yellow solid crashed out. The reaction was quenched by addition of aqueous NaHCO3. The aqueous layer was extracted with EtOAc (2×200 mL). The combined organic layer was dried (Na2SO4), filtered and concentrated under reduced pressure to give crude 1-(1-bromo-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-chloro-2-phenylethanone as a pale yellow solid (0.38 g, 90%). 1H NMR (400 MHz, DMSO-d6) δ11.08 (brs, 1H), 8.43 (s, 1H), 7.52-7.39 (m, 5H), 6.52 (s, 1H), 4.80 (m, 2H), 3.85 (m, 2H), 3.28 (m, 2H); LCMS [M+H]: 405. The product was used in the next step without any further purification.

Aufarbeitung

  1. customDuring the reaction a yellow solid
  2. customThe reaction was quenched by addition of aqueous NaHCO3
  3. extractionThe aqueous layer was extracted with EtOAc (2×200 mL)
  4. dry with materialThe combined organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-41e8d1bf5d954383a7772042261bcece
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263610B2

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