Tetrahydrofuran → 2-{4-[4-(4-[1,2,3]Triazol-1-yl-butyl)-benzenesulfonylmethyl]-oxazol-2-yl}-5-trifluoromethoxy-1H-indole

HRID 1392237

Reaktionsgleichung

Reaktionsgleichung von HRID 1392237
[CH2:1]([N:5]1[CH:9]=[CH:8][N:7]=[N:6]1)[CH2:2][CH:3]=[CH2:4].C1COCC1.Br[C:16]1[CH:21]=[CH:20][C:19]([S:22]([CH2:25][C:26]2[N:27]=[C:28]([C:31]3[NH:32][C:33]4[C:38]([CH:39]=3)=[CH:37][C:36]([O:40][C:41]([F:44])([F:43])[F:42])=[CH:35][CH:34]=4)[O:29][CH:30]=2)(=[O:24])=[O:23])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[N:5]1([CH2:1][CH2:2][CH2:3][CH2:4][C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH2:25][C:26]3[N:27]=[C:28]([C:31]4[NH:32][C:33]5[C:38]([CH:39]=4)=[CH:37][C:36]([O:40][C:41]([F:44])([F:42])[F:43])=[CH:35][CH:34]=5)[O:29][CH:30]=3)(=[O:24])=[O:23])=[CH:18][CH:17]=2)[CH:9]=[CH:8][N:7]=[N:6]1

Komponenten

8

Edukt 4

HCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 190682081-but-3-enyl-1H-[1,2,3]triazoleHCID 1363319632-[4-(4-bromo-benzenesulfonylmethyl)-oxazol-2-yl]-5-trifluoromethoxy-1H-indole

Produkt 1

HCID 1353998112-{4-[4-(4-[1,2,3]Triazol-1-yl-butyl)-benzenesulfonylmethyl]-oxazol-2-yl}-5-trifluoromethoxy-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 1-but-3-enyl-1H-[1,2,3]triazole (69 mg, 0.56 mmol) in THF (5 ml) 9-borabicyclo[3.3.1]nonane (0.5 M in THF, 2.46 ml, 1.23 mmol) was added dropwise at 0° C. and stirring continued for 2 h. This mixture was then added to a solution of 2-[4-(4-bromo-benzenesulfonylmethyl)-oxazol-2-yl]-5-trifluoromethoxy-1H-indole (0.28 g, 0.56 mmol), Pd(dppf)Cl2 (49 mg, 0.06 mmol) and aqueous cesium carbonate (0.56 ml, 3M) in DMF (5 ml) and stirred for 3 h at 70° C. Water (10 ml) was added and the mixture extracted with ethyl acetate (3×20 ml). The combined organic layers were washed with water and brine, dried over sodium sulfate and concentrated. The crude product was purified on silica gel (ethyl acetate) to yield 2-{4-[4-(4-[1,2,3]Triazol-1-yl-butyl)-benzenesulfonylmethyl]-oxazol-2-yl}-5-trifluoromethoxy-1H-indole as light yellow solid. Yield 24 mg (8%)

Aufarbeitung

  1. stirringstirred for 3 h at 70° C
  2. extractionthe mixture extracted with ethyl acetate (3×20 ml)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe crude product was purified on silica gel (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-cd0e8ac487304692b0f1a0f1b852a272
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07342030B2

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