Sodium Carbonate → 5-(6,7-Dihydropyrido[3,2-b]thieno[2,3-d]oxepin-9-yl)pyridin-2-nitrile

HRID 628020Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 628020
Br[C:2]1[S:15][C:5]2[C:6]3[N:14]=[CH:13][CH:12]=[CH:11][C:7]=3[O:8][CH2:9][CH2:10][C:4]=2[CH:3]=1.B1([C:25]2[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[N:27][CH:26]=2)OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.C(#N)C>[N:14]1[C:6]2[C:5]3[S:15][C:2]([C:25]4[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[N:27][CH:26]=4)=[CH:3][C:4]=3[CH2:10][CH2:9][O:8][C:7]=2[CH:11]=[CH:12][CH:13]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 164141882-Cyanopyridine-5-boronic acid pinacol esterHCID 579004919-Bromo-6,7-dihydropyrido[3,2-b]thieno[2,3-d]oxepine

Produkt 1

HCID 668690225-(6,7-Dihydropyrido[3,2-b]thieno[2,3-d]oxepin-9-yl)pyridin-2-nitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 80 mg (0.3 mmol) of 9-bromo-6,7-dihydro-pyrido[3,2-b]thieno[2,3-d]oxepine, 78.3 (0.34 mmol), 2-cyanopyridine-5-boronic acid pinacole ester, and 10 mg (0.014 mmol) of bis(triphenylphosphine)palladium (II) chloride in 0.35 ml (0.35 mmol) of aqueous 1 M solution of sodium carbonate and 4 ml of acetonitrile was degassed and microwaved on 200 Wt at 140° C. for 30 min. the reaction mixture was filtered through celite and partitioned between ethyl acetate and water. The organic layer was washed with water, brine dried over sodium sulfate and concentrated in vacuum. The residue was purified on a 4 g silica column eluting with 10% of methanol in dichloromethane to give 5-(6,7-dihydropyrido[3,2-b]thieno[2,3-d]oxepin-9-yl)pyridin-2-nitrile. Yield 27 mg (30%). MS: (ESI+) 306.1

Aufarbeitung

  1. customwas degassed
  2. custommicrowaved on 200 Wt at 140° C. for 30 min. the reaction mixture
  3. filtrationwas filtered through celite
  4. custompartitioned between ethyl acetate and water
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuum
  8. customThe residue was purified on a 4 g silica column
  9. washeluting with 10% of methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-b4dbfac0760d437ca2efd8477cc7f3b0
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309265B2

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