Water → methyl 2-(tert-butoxy)-2-[1-(3,4-dihydro-2H-1-benzopyran-6-yl)thieno[3,2-f]quinolin-2-yl]acetate

HRID 591019Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 591019
C(=O)([O-])[O-].[Na+].[Na+].O.Br[C:9]1[C:13]2=[C:14]3[C:19](=[CH:20][CH:21]=[C:12]2[S:11][C:10]=1[CH:22]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[C:23]([O:25][CH3:26])=[O:24])[N:18]=[CH:17][CH:16]=[CH:15]3.CC1(C)C(C)(C)OB([C:40]2[CH:41]=[C:42]3[C:47](=[CH:48][CH:49]=2)[O:46][CH2:45][CH2:44][CH2:43]3)O1>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:28]([O:27][CH:22]([C:10]1[S:11][C:12]2[C:13](=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]=[CH:17][CH:16]=[CH:15]3)[C:9]=1[C:40]1[CH:49]=[CH:48][C:47]2[O:46][CH2:45][CH2:44][CH2:43][C:42]=2[CH:41]=1)[C:23]([O:25][CH3:26])=[O:24])([CH3:31])([CH3:30])[CH3:29]

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 86717834Methyl 2-{1-bromothieno[3,2-f]quinolin-2-yl}-2-(tert-butoxy)acetate

Produkt 1

HCID 70818457methyl 2-(tert-butoxy)-2-[1-(3,4-dihydro-2H-1-benzopyran-6-yl)thieno[3,2-f]quinolin-2-yl]acetateAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Under argon atmosphere, sodium carbonate (15.7 mg, 0.15 mmol), water (0.8 mL), and methyl 2-{1-bromothieno[3,2-f]quinolin-2-yl}-2-(tert-butoxy)acetate (16i) (55 mg, 0.14 mmol) were added to a solution of 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman (38.5 mg, 0.15 mmol) in N,N-dimethylformamide (3 mL). The solution was degassed under argon and palladium tetrakis(triphenylphosphine) (47 mg, 0.04 mmol) was added. The mixture was heated at 100° C. for 4 hours. The mixture was then cooled at room temperature, water was added and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and evaporated under reduced pressure. The residue was purified by preparative TLC (cyclohexane/ethyl acetate 70/30) to afford the desired product (16j) (19 mg, 0.04 mmol, 31%).

Aufarbeitung

  1. customThe solution was degassed under argon
  2. temperatureThe mixture was then cooled at room temperature
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was purified by preparative TLC (cyclohexane/ethyl acetate 70/30)

Quellen und Nachweise

ORD-Eintrag
ord-44ec1765b5af4e0da350e6daa6753e03
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238026B2

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