3-Bromopyridine → 3-Benzothiazol-6-yl-1-pyridin-3-yl-4-trifluoromethyl-imidazolidin-2-one

HRID 80230

Reaktionsgleichung

Reaktionsgleichung von HRID 80230
[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH:14]([C:15]([F:18])([F:17])[F:16])[CH2:13][NH:12][C:11]3=[O:19])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.Br[C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1.CNC1CCCCC1NC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.C(OCC)(=O)C.O1CCOCC1>[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH:14]([C:15]([F:17])([F:18])[F:16])[CH2:13][N:12]([C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)[C:11]3=[O:19])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Komponenten

8

Edukt 4

HCID 122863-BromopyridineHCID 62657Potassium Phosphate, TribasicHCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamineHCID 596362031-Benzothiazol-6-yl-5-trifluoromethyl-imidazolidin-2-one

Produkt 1

HCID 498725583-Benzothiazol-6-yl-1-pyridin-3-yl-4-trifluoromethyl-imidazolidin-2-oneAusbeute 45,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Using the same reaction conditions and work up as described in Example 1, step-3,1-benzothiazol-6-yl-5-trifluoromethyl-imidazolidin-2-one (I-172b: 0.1 g, 0.0004 mol) was refluxed with 3-bromo-pyridine (0.085 g, 0.0005 mol), copper iodide (0.0076 g, 0.00004 mol), N,N′-dimethyl-cyclohexane-1,2-diamine (0.017 g, 0.00012 mol), potassium phosphate (0.22 g, 0.0012 mol) and 1,4-dioxane (20 mL) at 120° C. for 12 hours to afford the crude product. The reaction was monitored by TLC (100% ethyl acetate). Purification by column chromatography on silica gel (2% methanol in DCM) afforded 54 mg of the product (45.2% yield).

Aufarbeitung

  1. customthe same reaction conditions
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (2% methanol in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-dc31d96234044d42853fa7bc593206eb
Quelldatensatz
uspto-grants-2014_09
Patentnummer
USRE045173E1

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