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Ethyl Acetate → HCID 136101881, Verbindung

HRID 1091734
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1091734
Br[C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][C:6]1[C:7]2[C:8](=[C:13]([CH3:17])[NH:14][C:15]=2[CH3:16])[C:9](=[O:12])[NH:10][N:11]=1.C(N(C(C)C)C(C)C)C.CC[O:32][C:33](C)=[O:34]>CN(C)C1C=CN=CC=1.O1CCOCC1.O.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo].C(O[Pd]CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C)(=O)C>[CH3:16][C:15]1[NH:14][C:13]([CH3:17])=[C:8]2[C:7]=1[C:6]([CH2:5][C:4]1[CH:3]=[C:2]([CH:20]=[CH:19][CH:18]=1)[C:33]([OH:34])=[O:32])=[N:11][NH:10][C:9]2=[O:12]
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Komponenten

9

Edukt 3

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 1361018774-(3-bromobenzyl)-5,7-dimethyl-2,6-dihydro-1H-pyrrolo[3,4-d]pyridazin-1-one

Produkt 1

HCID 136101881HCID 136101881, VerbindungAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 142844-(Dimethylamino)pyridineKatalysator
HCID 98885Molybdenum carbonyl (Mo(CO)6)Katalysator
HCID 178476741HCID 178476741, VerbindungKatalysator
HCID 962WaterLösungsmittel2×
HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

4-(3-Bromobenzyl)-5,7-dimethyl-2,6-dihydro-1H-pyrrolo[3,4-d]pyridazin-1-one (50) (0.188 g, 0.57 mmol), molybdenum hexacarbonyl (0.224 g, 0.85 mmol), N,N-dimethylpyridin-4-amine (0.138 g, 1.13 mmol), N-ethyl-N-isopropylpropan-2-amine (0.197 mL, 1.13 mmol) and acetoxy(2-(dio-tolylphosphino)benzyl)palladium (0.027 g, 0.03 mmol) were suspended in a mixture of dioxane (2.0 mL) and water (2.0 mL) and sealed into a microwave tube. The reaction was heated to 150° C. for 30 minutes in the microwave reactor and cooled to room temperature. The reaction mixture was diluted with water (50 mL) and EtOAc (50 mL). The mixture was filtered through celite. The layers were separated and the aqueous was adjusted to pH2 with 2M HCl. The resulting precipitate was collected by filtration, washed with water (50 mL), Et2O (50 mL) and dried under vacuum to afford the desired material as a brown solid (0.200 g, >100% yield), which was used without further purification. 1H NMR (400.132 MHz, DMSO) δ 2.26 (3H, s), 2.51 (3H, s), 4.13 (2H, s), 7.39-7.48 (2H, m), 7.78 (2H, m), 11.08 (1H, s), 11.93 (1H, s), 12.86 (1H, s); m/z (LC-MS, ESI+), RT=1.41 min (M+H=298.08).

Aufarbeitung

  1. customsealed into a microwave tube
  2. temperaturecooled to room temperature
  3. filtrationThe mixture was filtered through celite
  4. customThe layers were separated
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with water (50 mL), Et2O (50 mL)
  7. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-2ea4038461644a488fb7a6c2de2bd87d
Quelldatensatz
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08129380B2

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