N-(2-(p-bromophenoxy)ethyl)pyrrolidine → HCID 59589976, Verbindung

HRID 1971607

Reaktionsgleichung

Reaktionsgleichung von HRID 1971607
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[N:16]4[N:17]=[C:18]([NH2:20])[N:19]=[C:15]4[CH:14]=[CH:13][C:12]=3[O:21][CH3:22])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.Br[C:24]1[CH:37]=[CH:36][C:27]([O:28][CH2:29][CH2:30][N:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)=[CH:26][CH:25]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CC(C)([O-])C.[Na+]>CC(N(C)C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].O1CCOCC1>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[N:16]4[N:17]=[C:18]([NH:20][C:24]5[CH:25]=[CH:26][C:27]([O:28][CH2:29][CH2:30][N:31]6[CH2:32][CH2:33][CH2:34][CH2:35]6)=[CH:36][CH:37]=5)[N:19]=[C:15]4[CH:14]=[CH:13][C:12]=3[O:21][CH3:22])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Komponenten

8

Edukt 4

HCID 70657N-(2-(p-bromophenoxy)ethyl)pyrrolidineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxideHCID 595896845-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-6-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

Produkt 1

HCID 59589976HCID 59589976, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 31374DimethylacetamideKatalysatorHCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

In a microwave vial, 5-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-6-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (0.05 g, 0.17 mmol), 1-[2-(4-bromophenoxy)ethyl]-pyrrolidine (0.068 g, 0.251 mmol), bis(dibenzylideneacetone)palladium (0.005 g, 0.008 mmol), Xantphos (0.01 g, 0.017 mmol) and sodium tert-butoxide (0.033 g, 0.335 mmol) were added successively. Dioxane (1.2 mL) and dimethylacetamide (2 drops) were added and the vial was sealed and heated in the microwave (150° C., 10 min). The crude was purified using an SCX cartridge, by washing with methanol and releasing the compound with 2M ammonia in methanol. After concentration under reduced pressure, the crude was purified by preparatory LCMS. LCMS Method: 2: RT: 2.52 min, MI: 488 [M+1].

Aufarbeitung

  1. customthe vial was sealed
  2. customThe crude was purified
  3. washby washing with methanol
  4. concentrationAfter concentration under reduced pressure
  5. customthe crude was purified by preparatory LCMS

Quellen und Nachweise

ORD-Eintrag
ord-03eab5ab938e4f9aaeb9115a72607a58
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08431596B2

Verknüpfte Notizen

Wird geladen…