Cesium carbonate → HCID 42644651, Verbindung

HRID 390710

Reaktionsgleichung

Reaktionsgleichung von HRID 390710
[CH3:1][C:2]1[S:6][C:5]([NH:7][C:8]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:9])=[N:4][CH:3]=1.ClC1C=C2C(N=CC=C2)=C2C=1C=CC=N2.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:36]([C:43]1[CH:48]=[CH:47][C:46](Br)=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[OH-].[NH4+].O>CN1CCCC1=O>[CH2:36]([C:37]1[CH:42]=[CH:41][C:40]([N:4]2[CH:3]=[C:2]([CH3:1])[S:6]/[C:5]/2=[N:7]\[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:9])=[CH:39][CH:38]=1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Komponenten

7

Edukt 5

HCID 10796Cesium carbonateHCID 778655-Chloro-1,10-phenanthrolineHCID 2360001-Benzyl-4-bromobenzeneHCID 47197229HCID 47197229, VerbindungHCID 86589665Water ammonium hydroxide

Produkt 1

HCID 42644651HCID 42644651, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

In a 4 mL vial charged with a stir bar, N-(5-methyl-1,3-thiazol-2-yl)pyrrolidine-1-carboxamide (58 mg, 0.27 mmol) was added, followed by copper(I) trifluoromethanesulfonate benzene complex (27 mg, 0.05 mmol), 5-chloro-1,10-phenanthroline (23 mg, 0.11 mmol) and cesium carbonate (97 mg, 0.3 mmol). A loose cap with septum was placed on the vial, and the vial was placed under vacuum in a vacuum oven for 30 minutes. The solid mixture was purged with nitrogen gas a couple of times. Then, 1-benzyl-4-bromobenzene (74 mg, 0.3 mmol) dissolved in 1-methyl-2-pyrrolidinone (1.0 mL) was added to the mixture. The vial was capped and placed on a heater/stirrer and heated to 120° C. overnight. Then 1 mL of a solution of concentrated ammonium hydroxide/water (1:2) was added. The reaction was filtered and concentrated to dryness. The residue was purified by reverse phase HPLC (C8, gradient 10-100% acetonitrile/water/0.1% trifluoroacetic acid).

Aufarbeitung

  1. additionIn a 4 mL vial charged with a stir bar
  2. customA loose cap with septum
  3. customThe solid mixture was purged with nitrogen gas a couple of times
  4. additionwas added to the mixture
  5. customThe vial was capped
  6. customplaced on a heater/stirrer
  7. filtrationThe reaction was filtered
  8. concentrationconcentrated to dryness
  9. customThe residue was purified by reverse phase HPLC (C8, gradient 10-100% acetonitrile/water/0.1% trifluoroacetic acid)

Quellen und Nachweise

ORD-Eintrag
ord-fa10bb1a4b5247e1a0c9653f6ac5004d
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383657B2

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