Cesium fluoride → 4-(3-(3-Carboxypropanoyl)-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-7-yl)benzoic acid

HRID 553537Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 553537
C([O:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:23]=[C:22]3[C:17]([C:18]([OH:30])=[C:19]([C:26]([O:28]C)=O)[C:20](=[O:25])[N:21]3[CH3:24])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)=[O:7])(C)(C)C.BrC1C=C2C([C:36](O)=[C:37]([C:44]([O:46]C)=[O:45])C(=O)N2C)=CC=1.C(OC(C1C=CC(B(O)O)=CC=1)=O)(C)(C)C.[F-].[Cs+]>CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CO>[C:44]([CH2:37][CH2:36][C:26]([C:19]1[C:20](=[O:25])[N:21]([CH3:24])[C:22]2[C:17]([C:18]=1[OH:30])=[CH:16][CH:15]=[C:14]([C:11]1[CH:12]=[CH:13][C:8]([C:6]([OH:5])=[O:7])=[CH:9][CH:10]=1)[CH:23]=2)=[O:28])([OH:46])=[O:45]

Komponenten

8

Edukt 4

HCID 25953Cesium fluorideHCID 2773301(4-((Tert-butoxy)carbonyl)phenyl)boronic acidHCID 59340050Methyl 7-bromo-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylateHCID 67410169Methyl 7-(4-(tert-butoxycarbonyl)phenyl)-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate

Produkt 1

HCID 547473424-(3-(3-Carboxypropanoyl)-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-7-yl)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Methyl 7-(4-(tert-butoxycarbonyl)phenyl)-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate. To a mixture of methyl 7-bromo-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate (Method 7) (3.82 g, 12.2 mmol), 4-(tert-butoxycarbonyl)phenylboronic acid (2.72 g, 12.2 mmol), cesium fluoride (5.58 g, 36.7 mmol), and tetrakis(triphenylphosphine)palladium [0] (0.424 g, 0.367 mmol) in a vial, was added MeOH (61 mL). The vial was sealed and heated at 80° C. for 2 hours. The reaction mixture was then cooled, diluted with 200 mL of EtOAc, added to a separatory funnel, partitioned with sodium bicarbonate (saturated, aqueous), washed 2 times with 75 mL of sodium bicarbonate (saturated, aqueous), separated, dried over sodium sulfate, and concentrated via rotary evaporation to give the product. The resulting product was purified via flash chromatography (silica gel) to provide the title compound as an off-white solid.

Aufarbeitung

  1. customThe vial was sealed
  2. temperatureThe reaction mixture was then cooled
  3. additionadded to a separatory funnel
  4. custompartitioned with sodium bicarbonate (saturated, aqueous)
  5. washwashed 2 times with 75 mL of sodium bicarbonate (saturated, aqueous)
  6. customseparated
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated via rotary evaporation
  9. customto give the product
  10. customThe resulting product was purified via flash chromatography (silica gel)

Quellen und Nachweise

ORD-Eintrag
ord-b6868b999e1345f08a9f3686062a71f8
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08048894B2

Notizen zur Reaktion

Wird geladen…