Cesium carbonate → 5-(2,6-Dimethoxyphenyl)-1-(4-((4-methylthiazol-2-yl)oxy)benzyl)pyrrolidin-2-one

HRID 594677Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 594677
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH:11]1[N:15]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[C:14](=[O:24])[CH2:13][CH2:12]1.Br[C:26]1[S:27][CH:28]=[C:29]([CH3:31])[N:30]=1.C([O-])([O-])=O.[Cs+].[Cs+].CC(C)(C(=O)CC(=O)C(C)(C)C)C>CN1C(=O)CCC1.Cl[Cu].C1(C)C=CC=CC=1.CCOC(C)=O.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH:11]1[N:15]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([O:23][C:26]3[S:27][CH:28]=[C:29]([CH3:31])[N:30]=3)=[CH:21][CH:22]=2)[C:14](=[O:24])[CH2:13][CH2:12]1

Komponenten

10

Edukt 4

HCID 10796Cesium carbonateHCID 707002,2,6,6-Tetramethyl-3,5-heptanedioneHCID 5515412-Bromo-4-methyl-1,3-thiazoleHCID 690819375-(2,6-Dimethoxyphenyl)-1-(4-hydroxybenzyl)pyrrolidin-2-one

Produkt 1

HCID 690826245-(2,6-Dimethoxyphenyl)-1-(4-((4-methylthiazol-2-yl)oxy)benzyl)pyrrolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 62652Cuprous chlorideKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

In a microwave tube, a mixture of 5-(2,6-dimethoxyphenyl)-1-(4-hydroxybenzyl)pyrrolidin-2-one (prepared as described in example 282; 60 mg; 0.18 mmol), commercially available 2-bromo-4-methylthiazole (65 mg; 0.36 mmol), Cs2CO3 (66 mg; 0.20 mmol), CuCl (9 mg; 0.09 mmol), and commercially available 2,2,6,6-tetramethylheptane-3,5-dione (34 mg; 0.18 mmol) in anh. NMP (1 ml) was sealed and irradiated by microwave (175° C.; 10 min.). Water (1 ml), AcOEt (2 ml), and toluene (1 ml) were added, and the resulting suspension was filtered over a pad of celite. The separated organic layer was dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Subsequent purification by preparative HPLC afforded the target compound. LC-MS (conditions A): tR=0.83 min.; [M+H]+: 424.98 g/mol.

Aufarbeitung

  1. customwas sealed
  2. customirradiated by microwave (175° C.; 10 min.)
  3. filtrationthe resulting suspension was filtered over a pad of celite
  4. dry with materialThe separated organic layer was dried over anh. MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customSubsequent purification by preparative HPLC
  8. customafforded the target compound

Quellen und Nachweise

ORD-Eintrag
ord-8ef7e825d1c84cb3be3d23f167fca88e
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242970B2

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