Methanol → Tasipimidine

HRID 1771417Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1771417
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][O:6][CH:7]2[C:12]1[NH:13][CH2:14][CH2:15][N:16]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.[C:38]([O-])([O-])=[O:39].[Cs+].[Cs+].CO>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[CH3:38][O:39][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][O:6][CH:7]2[C:12]1[NH:13][CH2:14][CH2:15][N:16]=1

Komponenten

7

Edukt 4

HCID 887MethanolHCID 10796Cesium carbonateHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 717669082-(5-bromoisochroman-1-yl)-4,5-dihydro-1H-imidazole

Produkt 1

HCID 71767208Tasipimidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

To a mixture of 2-(5-bromoisochroman-1-yl)-4,5-dihydro-1H-imidazole (200 mg), 2-(di-t-butylphosphino)biphenyl (5.31 mg), palladium(II)acetate (3.19 mg) and Cs2CO3 (348 mg) was added methanol (1 ml) and toluene (2 ml). The mixture was degassed with N2 and then heated for 40 min at 120° C. and 30 min at 130° C. Alternatively, other Pd-ligand complexes and reaction conditions can be applied in the C—O formation. The title compound was purified by using separation methods E and G. (Yield 5 mg).

Aufarbeitung

  1. customThe mixture was degassed with N2
  2. customAlternatively, other Pd-ligand complexes and reaction conditions
  3. customThe title compound was purified
  4. customseparation methods E and G

Quellen und Nachweise

ORD-Eintrag
ord-e5270498fdaa4c2cbcbcef4f0caff6a7
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09249127B2

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