7-Bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one → 7-bromo-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepine

HRID 1365057Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1365057
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=O)[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])[C:6]=2[CH:20]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][CH2:10][CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])[C:6]=2[CH:20]=1

Komponenten

4

Edukt 2

HCID 129470247-Bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-oneHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 577324247-bromo-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepineAusbeute 52,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A round-bottomed flask was charged with 7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one (500 mg) and tetrahydrofuran (20 mL). To this mixture was added lithium aluminum hydride (1.8 mL of 1M solution in tetrahydrofuran). The reaction was stirred overnight at room temperature, then quenched with water and 10% sodium hydroxide. The quenched mixture was filtered through Celite and the filter was washed with ethyl acetate. The filtrate was dried over magnesium sulfate, filtered and concentrated to an oil. Silica gel purification provided 7-bromo-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepine (250 mg) as a yellow powder. H1 NMR (d6-dmso): 7.43-7.50 (m, 1H), 7.40 (dt, 1H), 7.18-7.28 (m, 3H), 6.75-6.81 (m, 2H), 6.71 (d, 1H), 3.95 (m, 2H), 3.49 (m, 2H). Mass (ES+)=319.1 (100%).

Aufarbeitung

  1. customquenched with water and 10% sodium hydroxide
  2. filtrationThe quenched mixture was filtered through Celite
  3. washthe filter was washed with ethyl acetate
  4. dry with materialThe filtrate was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to an oil
  7. customSilica gel purification

Quellen und Nachweise

ORD-Eintrag
ord-1de3bd6af1a74c39a5c20a8966452836
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07888503B2

Notizen zur Reaktion

Wird geladen…