Water → methyl 2-(tert-butoxy)-2-[5-(3,4-dihydro-2H-1-benzopyran-6-yl)-2-phenyl-1,3-thiazol-4-yl]acetate

HRID 590972Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 590972
C(=O)([O-])[O-].[Na+].[Na+].O.CC1(C)C(C)(C)OB([C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][CH:25]=2)[O:22][CH2:21][CH2:20][CH2:19]3)O1.Br[C:28]1[S:32][C:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[N:30][C:29]=1[CH:39]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])[C:40]([O:42][CH3:43])=[O:41]>CN(C)C=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[C:45]([O:44][CH:39]([C:29]1[N:30]=[C:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[S:32][C:28]=1[C:16]1[CH:25]=[CH:24][C:23]2[O:22][CH2:21][CH2:20][CH2:19][C:18]=2[CH:17]=1)[C:40]([O:42][CH3:43])=[O:41])([CH3:48])([CH3:46])[CH3:47]

Komponenten

7

Edukt 4

HCID 962Water2×HCID 10340Sodium CarbonateHCID 438110342-(3,4-dihydro-2H-1-benzopyran-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 70819454Methyl 2-(5-bromo-2-phenyl-1,3-thiazol-4-yl)-2-(tert-butoxy)acetate

Produkt 1

HCID 70855246methyl 2-(tert-butoxy)-2-[5-(3,4-dihydro-2H-1-benzopyran-6-yl)-2-phenyl-1,3-thiazol-4-yl]acetateAusbeute 70,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Under a nitrogen atmosphere, sodium carbonate (8.5 mg, 0.08 mmol), water (500 μL), palladium tetrakis(triphenylphosphine) (13 mg, 0.012 mmol) and 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman (21 mg, 0.078 mmol) were added to a solution of methyl 2-(5-bromo-2-phenyl-1,3-thiazol-4-yl)-2-(tert-butoxy)acetate (30 mg, 0.078 mmol) in N,N-dimethylformamide (2 mL). The mixture was heated at 120° C. for 2 hours. The mixture was then cooled at room temperature and water (10 mL) was added. The aqueous layer was extracted with ethyl acetate (2×10 mL). The organic layer was washed with brine (10 mL), dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10) to afford the desired product (6d) as a white solid (24 mg, 0.055 mmol, 70%).

Aufarbeitung

  1. temperatureThe mixture was then cooled at room temperature
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×10 mL)
  3. washThe organic layer was washed with brine (10 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10)

Quellen und Nachweise

ORD-Eintrag
ord-46e6e992c5264b3c8b4a8f8bf0762dd6
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238026B2

Notizen zur Reaktion

Wird geladen…