Dimethylformamide → HCID 11492286, Verbindung

HRID 1365070Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1365070
Br[C:2]1[CH:3]=[CH:4][C:5]2[NH:11][CH2:10][CH2:9][N:8]=[CH:7][C:6]=2[CH:12]=1.[N:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>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.O>[N:13]1[CH:18]=[CH:17][C:16]([C:2]2[CH:3]=[CH:4][C:5]3[NH:11][CH2:10][CH2:9][N:8]=[CH:7][C:6]=3[CH:12]=2)=[CH:15][CH:14]=1

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 57732439HCID 57732439, Verbindung

Produkt 1

HCID 11492286HCID 11492286, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

A 20 mL microwave tube was charged 7-bromo-2,3-dihydro-1H-1,4-benzodiazepine (115 mg), 4-pyridylboronic acid (2 equiv), potassium carbonate (2 equiv), dichlorobis(triphenyl-phosphine)palladium(II) (10 mol %), DMF (3.5 mL) and water (0.7 mL) then heated to 160° C. for 360 s using microwave irradiation. The reaction was concentrated to dryness and the residue was taken up in water then extracted with ethyl acetate/tetrahydrofuran (3:1). The organic extracts were combined and dried over sodium sulfate. The drying salts were removed by filtration and the filtrate was concentrated. The residue was triturated with diethyl ether and the resulting solids were collected on filter. Recrystallization from hot tetrahydrofuran provided 7-(4-pyridinyl)-2,3-dihydro-1H-1,4-benzodiazepine as a tan powder (9 mg). H1 NMR (d6-dmso): 8.49 (d, 2H), 8.23 (s, 1H), 7.85 (d, 1H), 7.62 (m, 3H), 7.29 (br t, 1H), 6.80 (d, 1H), 3.85 (m, 2H), 3.25 (m, 2H). Mass (ES+)=224.2 (100%).

Aufarbeitung

  1. custommicrowave irradiation
  2. concentrationThe reaction was concentrated to dryness
  3. extractionthen extracted with ethyl acetate/tetrahydrofuran (3:1)
  4. dry with materialdried over sodium sulfate
  5. customThe drying salts were removed by filtration
  6. concentrationthe filtrate was concentrated
  7. customThe residue was triturated with diethyl ether
  8. customthe resulting solids were collected
  9. filtrationon filter
  10. customRecrystallization from hot tetrahydrofuran

Quellen und Nachweise

ORD-Eintrag
ord-878759534c9e48b2be7ccc3a95f0f048
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07888503B2

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