3-(Bromomethyl)-4-fluorobenzonitrile → 4-Fluoro-3-(9-fluoro-10-methyl-6-oxo-6H-5-oxa-4,7-diaza-benzo[c]fluoren-7-ylmethyl)-benzonitrile

HRID 1098657Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1098657
[F:1][C:2]1[C:3]([CH3:20])=[CH:4][C:5]2[C:6]3[C:7]4[CH:19]=[CH:18][CH:17]=[N:16][C:8]=4[O:9][C:10](=[O:15])[C:11]=3[NH:12][C:13]=2[CH:14]=1.Br[CH2:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][C:30]=1[F:31])[C:26]#[N:27]>CN(C=O)C.C(OCC)(=O)C>[F:31][C:30]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][C:23]=1[CH2:22][N:12]1[C:11]2[C:10](=[O:15])[O:9][C:8]3[N:16]=[CH:17][CH:18]=[CH:19][C:7]=3[C:6]=2[C:5]2[CH:4]=[C:3]([CH3:20])[C:2]([F:1])=[CH:14][C:13]1=2

Komponenten

5

Edukt 2

HCID 162272363-(Bromomethyl)-4-fluorobenzonitrileHCID 581324399-Fluoro-10-methyl-7H-5-oxa-4,7-diaza-benzo[c]fluoren-6-one

Produkt 1

HCID 581327234-Fluoro-3-(9-fluoro-10-methyl-6-oxo-6H-5-oxa-4,7-diaza-benzo[c]fluoren-7-ylmethyl)-benzonitrileAusbeute 80,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 9-Fluoro-10-methyl-7H-5-oxa-4,7-diaza-benzo[c]fluoren-6-one 1G (167 mg, 0.622 mmol) in DMF (3.0 mL) was added 3-Bromomethyl-4-fluoro-benzonitrile (160.0 mg, 0.747 mmol) and CsCO3 (243 mg, 0.747 mmol) at room temperature and the reaction mixture was allowed to stir overnight. The reaction mixture was diluted with ethyl acetate, washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The concentrated crude was purified using chromatography over SiO2 using 0 to 30% ethyl acetate in hexane to provide 4-Fluoro-3-(9-fluoro-10-methyl-6-oxo-6H-5-oxa-4,7-diaza-benzo[c]fluoren-7-ylmethyl)-benzonitrile 1H (200 mg, 80%). M.S. found for C23H13F2N3O2: 402.9 (M+H)+.

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. concentrationThe concentrated crude
  6. customwas purified

Quellen und Nachweise

ORD-Eintrag
ord-0479143dc2cb464a8523d5887260b7ee
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143305B2

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