Cesium carbonate → HCID 60042063, Verbindung

HRID 2383396Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2383396
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@H:3]([NH:9][C:10]([C:12]1[C:16]3[CH:17]=[CH:18][C:19](Br)=[CH:20][C:15]=3S[N:13]=1)=[O:11])[CH2:2]2.C[C:23]1(C)[C:36]2[CH:35]=[CH:34][CH:33]=[C:32](P(C3C=CC=CC=3)C3C=CC=CC=3)[C:31]=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.[C:64](=[O:67])([O-])[O-].[Cs+].[Cs+].[C:70](=[NH:83])([C:77]1[CH:82]=[CH:81]C=CC=1)C1C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@H:3]([NH:9][C:10]([C:12]1[C:16]3[C:15](=[CH:20][CH:19]=[C:18]([N:1]4[CH2:2][CH2:3][CH:64]([O:67][CH2:23][C:36]5[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=5)[CH2:6]4)[CH:17]=3)[N:83]([CH2:70][CH:77]3[CH2:82][CH2:81]3)[N:13]=1)=[O:11])[CH2:2]2

Komponenten

6

Edukt 4

HCID 10796Cesium carbonateHCID 136809Benzophenone imineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 10044409HCID 10044409, Verbindung

Produkt 1

HCID 60042063HCID 60042063, VerbindungAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 167845palladium(II) acetateKatalysator

Versuchsvorschrift

The mixture of N-[(3S)-1-azabicyclo[2.2.2]oct-3-yl]-6-bromo-1,2-benzisothiazole-3-carboxamide (6.30 mmol), palladium acetate (1.00 mmol), and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (Xantphos) (0.700 mmol) was evacuated and back-fill with Ar gas. The solids were diluted with tetrahydrofuran (150 mL) and treated with cesium carbonate (7.00 mmol) and benzophenone imine (6.80 mmol). The reaction mixture was heated at reflux for 16 h. The reaction mixture was concentrated and redissolved in a mixture of tetrahydrofuran (90 mL) and 3 N hydrochloric acid (30 mL). The reaction mixture was maintained for 2 h and was concentrated. The residue was purified by chromatography using a mixture of 70/30/1 ethyl acetate/methanol/ammonium hydroxide, thus providing the aniline in 79% yield. The aniline was used directly in subsequent reactions.

Aufarbeitung

  1. customwas evacuated and back-fill with Ar gas
  2. additionThe solids were diluted with tetrahydrofuran (150 mL)
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux for 16 h
  5. concentrationThe reaction mixture was concentrated
  6. dissolutionredissolved in a mixture of tetrahydrofuran (90 mL) and 3 N hydrochloric acid (30 mL)
  7. temperatureThe reaction mixture was maintained for 2 h
  8. concentrationwas concentrated
  9. customThe residue was purified by chromatography
  10. additiona mixture of 70/30/1 ethyl acetate/methanol/ammonium hydroxide

Quellen und Nachweise

ORD-Eintrag
ord-73e295f7ad8f469eba95bcdb0b9235db
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263619B2

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