Sodium Carbonate → 5-(2-fluorophenyl)-7-(4-pyridinyl)-2,3-dihydro-1H-1,4-benzodiazepine

HRID 1365058Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1365058
Br[C:2]1[CH:3]=[CH:4][C:5]2[NH:11][CH2:10][CH2:9][N:8]=[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[F:18])[C:6]=2[CH:19]=1.[N:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C)C=O>[F:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:7]1[C:6]2[CH:19]=[C:2]([C:23]3[CH:24]=[CH:25][N:20]=[CH:21][CH:22]=3)[CH:3]=[CH:4][C:5]=2[NH:11][CH2:10][CH2:9][N:8]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 577324247-bromo-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepine

Produkt 1

HCID 115587405-(2-fluorophenyl)-7-(4-pyridinyl)-2,3-dihydro-1H-1,4-benzodiazepineAusbeute 41,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A 5-mL microwave tube was charged with 7-bromo-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepine (85 mg), 4-pyridylboronic acid (100 mg), dichlorobis(triphenylphosphine)palladium(II) (20 mg), dimethylformamide (3.5 mL) and a saturated solution of sodium carbonate (0.5 mL). The reaction was heated to 150° C. for 360 seconds using microwave irradiation. The reaction was concentrated to dryness and the residue was taken up in water and extracted with ethyl acetate. The organic extracts were combined and dried over magnesium sulfate. The drying agent was filtered and the filtrate was concentrated to an oil. Silica gel purification provided the title compound (5-(2-fluorophenyl)-7-(4-pyridinyl)-2,3-dihydro-1H-1,4-benzodiazepine, 35 mg) as an off-white crystalline solid. H1 NMR (d6-dmso): 8.40 (d, 2H), 7.57 (dd, 1H), 7.44 (t, 2H), 7.25 (m, 3H), 7.18 (m, 1H), 7.12 (m, 1H), 6.99 (br t, 1H), 6.85 (d, 1H), 3.98 (m, 2H), 3.54 (m, 2H). Mass (ES+)=318.2 (100%).

Aufarbeitung

  1. custommicrowave irradiation
  2. concentrationThe reaction was concentrated to dryness
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe drying agent was filtered
  6. concentrationthe filtrate was concentrated to an oil
  7. customSilica gel purification

Quellen und Nachweise

ORD-Eintrag
ord-9394e1a7f11a4ed794c72981fa589c9d
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07888503B2

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