Triethylamine → HCID 67111749, Verbindung

HRID 1177550Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1177550
C(N(CC)CC)C.[O:8]1[CH2:13][CH2:12][CH2:11][O:10][CH:9]1[C:14]1[CH:19]=[CH:18][C:17]([C:20]2[S:21][C:22]3[CH:28]=[C:27](Br)[CH:26]=[CH:25][C:23]=3[N:24]=2)=[C:16]([F:30])[CH:15]=1.C[CH2:32][O:33][C:34](C)=[O:35]>CN(C=O)C.C1COCC1.CO>[O:8]1[CH2:13][CH2:12][CH2:11][O:10][CH:9]1[C:14]1[CH:19]=[CH:18][C:17]([C:20]2[S:21][C:22]3[CH:28]=[C:27]([C:34]([O:33][CH3:32])=[O:35])[CH:26]=[CH:25][C:23]=3[N:24]=2)=[C:16]([F:30])[CH:15]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 671120772-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-6-bromobenzo[d]thiazole

Produkt 1

HCID 67111749HCID 67111749, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 86634690HCID 86634690, VerbindungLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

Triethylamine (0.32 mL, 2.28 mmol), 1,3-(bis[diphenylphosphino]propane) dichloropalladium(II) (0.051 g, 0.076 mmol), and 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-6-bromobenzo[d]thiazole (0.75 g, 1.90 mmol) were mixed in DMF:THF:MeOH (2:7:2, 11 mL total volume) in a heavy-walled pressure tube. The tube was placed under CO atmosphere (20 psi) and then heated to 95° C. for 16 h. The mixture was cooled to RT and EtOAc (5 mL) was added. The suspension was filtered and the collected solid was washed with EtOAc. The solid obtained was then partitioned between DCM and water, the layers were separated, and the organic layer was dried (MgSO4) and concentrated under vacuum to give methyl 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)benzo[d]thiazole-6-carboxylate as a white solid.

Aufarbeitung

  1. temperatureThe mixture was cooled to RT
  2. filtrationThe suspension was filtered
  3. washthe collected solid was washed with EtOAc
  4. customThe solid obtained
  5. customwas then partitioned between DCM and water
  6. customthe layers were separated
  7. dry with materialthe organic layer was dried (MgSO4)
  8. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-a7fd57d762c940adb4d23427f774e080
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842685B2

Notizen zur Reaktion

Wird geladen…