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Potassium Carbonate → ethyl 2-(4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)acetate

HRID 2366862
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2366862
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[CH3:14][CH:15]([O:17][C:18](=[O:43])[NH:19][C@H:20]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27](B3OC(C)(C)C(C)(C)O3)[CH:28]=2)[N:23]([C:39](=[O:41])[CH3:40])[C@@H:22]([CH3:42])[CH2:21]1)[CH3:16].C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>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>[C:39]([N:23]1[C:24]2[C:29](=[CH:28][C:27]([C:2]3[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=3)=[CH:26][CH:25]=2)[C@H:20]([NH:19][C:18]([O:17][CH:15]([CH3:16])[CH3:14])=[O:43])[CH2:21][C@@H:22]1[CH3:42])(=[O:41])[CH3:40]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 7020609Ethyl 2-(4-bromophenyl)acetateHCID 681853941-Methylethyl [(cis)-1-acetyl-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydro-4-quinolinyl]carbamate

Produkt 1

HCID 68185396ethyl 2-(4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)acetate
Ausbeute 59,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A flask was charged with ethyl (4-bromophenyl)acetate (0.174 mL, 1.000 mmol), 1-methylethyl[(2S,4R)-1-acetyl-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation, see Intermediate 52) (416 mg, 1 mmol), potassium carbonate (415 mg, 3.00 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (73.2 mg, 0.100 mmol) then filled with 1,4-dioxane (6 mL) and water (2 mL) and flushed with nitrogen. The resulting mixture was stirred under microwave irradiation at 120° C. for 30 min then cooled to room temperature. Most of the 1,4-dioxane was removed in vacuo and the residue was partitioned between AcOEt and water. The layers were separated and the aqueous phase was extracted with AcOEt. The combined organic phases were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue by SP4 on a 25 G silica cartridge (gradient: 5 to 25% of (10% MeOH in DCM) in DCM) gave ethyl {4-[(2S,4R)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]phenyl}acetate (270 mg, 0.597 mmol, 59.7% yield).

Aufarbeitung

  1. customfor a preparation
  2. customflushed with nitrogen
  3. temperaturethen cooled to room temperature
  4. customMost of the 1,4-dioxane was removed in vacuo
  5. customthe residue was partitioned between AcOEt and water
  6. customThe layers were separated
  7. extractionthe aqueous phase was extracted with AcOEt
  8. washThe combined organic phases were washed with brine
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated in vacuo
  11. customPurification of the residue by SP4 on a 25 G silica cartridge (gradient: 5 to 25% of (10% MeOH in DCM) in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-a68860216d5c4b0ea6da6d8d40257a35
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08697725B2

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