Potassium Carbonate → HCID 44480908, Verbindung

HRID 1521575Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1521575
Br[C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH2:9][CH2:8][CH2:7][C:6]=2[CH:13]=1.[N:14]1[CH:19]=[CH:18][CH:17]=[C:16](B(O)O)[CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl>[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:2]2[CH:3]=[CH:4][C:5]3[NH:11][C:10](=[O:12])[CH2:9][CH2:8][CH2:7][C:6]=3[CH:13]=2)[CH:15]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 149781117-Bromo-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one

Produkt 1

HCID 44480908HCID 44480908, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)Katalysator

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A sealable tube containing the title compound from Example 2 Step C (0.300 g, 1.25 mmol), 3-pyridylboronic acid (0.200 g, 1.62 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (0.018 g, 0.025 mmol) and potassium carbonate (0.368 g, 3.75 mmol) was flushed with nitrogen before tort-butanol (14.0 mL) and water (1.6 mL) were added. It was flushed again with nitrogen, sealed tightly and heated to 100° C. overnight. The reaction was then cooled to room temperature, poured into saturated aqueous sodium chloride solution and extracted with ethyl acetate. The organic extracts were combined, washed with water, dried over sodium sulfate, filtered and concentrated. Purification by flash chromatography on silica gel (0-12% methanol in ethyl acetate) provided the title compound: LCMS m/z 239.09 [M+H]+; 1H NMR (500 MHz, CD3OD) δ 8.72 (s, 1H), 8.46 (d, J=4.2 Hz, 1H), 7.86 (ddd, J=1.8, 1.9, 8.0 Hz, 1H), 7.41-7.39 (m, 2H), 7.35 (dd, J=4.8, 7.9 Hz, 1H), 7.04 (d, J=7.9 Hz, 1H), 2.81 (t, J=7.2 Hz, 2H), 2.35-2.31 (m, 2H), 2.26-2.20 (m, 2H).

Aufarbeitung

  1. customwas flushed with nitrogen before tort-butanol (14.0 mL) and water (1.6 mL)
  2. additionwere added
  3. customIt was flushed again with nitrogen
  4. customsealed tightly
  5. temperatureThe reaction was then cooled to room temperature
  6. additionpoured into saturated aqueous sodium chloride solution
  7. extractionextracted with ethyl acetate
  8. washwashed with water
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customPurification by flash chromatography on silica gel (0-12% methanol in ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-273846544b8345d9a46c240baef56feb
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073929B2

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