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Cesium fluoride → 3-(5-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)pyridin-2-yloxy)-N,N-dimethylpropan-1-amine

HRID 418728
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Reaktionsgleichung

Reaktionsgleichung von HRID 418728
Br[C:2]1[S:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][C:8]=2[O:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=2[F:21])[CH:3]=1.[CH3:22][N:23]([CH3:43])[CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31](B2OC(C)(C)C(C)(C)O2)=[CH:30][N:29]=1.[F-].[Cs+].C(=O)(O)[O-].[Na+]>COCCOC.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>[F:21][C:13]1[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=[CH:17][C:12]=1[O:11][C:8]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:3]=[C:2]([C:31]3[CH:32]=[CH:33][C:28]([O:27][CH2:26][CH2:25][CH2:24][N:23]([CH3:22])[CH3:43])=[N:29][CH:30]=3)[S:10][C:9]=12
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Komponenten

8

Edukt 4

HCID 25953Cesium fluorideHCID 516892Sodium BicarbonateHCID 17998906N,N-Dimethyl-3-((5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)oxy)propan-1-amineHCID 594245212-Bromo-7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine

Produkt 1

HCID 587903463-(5-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)pyridin-2-yloxy)-N,N-dimethylpropan-1-amine
Ausbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

Bromothienopyridine 50 (1.22 g, 3.30 mmol), N,N-dimethyl-3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yloxy)propan-1-amine (1.15 g, 3.76 mmol), and tetrakis(triphenylphosphine)palladium (0.14 g, 0.12 mmol) were dissolved in dry DME (100 mL). Cesium fluoride (1.51 g, 10.0 mmol) and sodium bicarbonate (0.81 g, 9.6 mmol) were dissolved in water (5 ml each) and added to the reaction mixture, which was degassed with a stream of N2, then heated to reflux for 4 h, cooled, and concentrated. The residue was partitioned between ethyl acetate and water. The organic phase was collected, washed with brine, dried (anhydrous MgSO4), filtered, and concentrated. The resulting orange solid was triturated with ether to provide 379 (1.12 g, 75% yield). LRMS (M+H): 469.2.

Aufarbeitung

  1. additionadded to the reaction mixture, which
  2. customwas degassed with a stream of N2
  3. temperatureheated
  4. temperatureto reflux for 4 h
  5. temperaturecooled
  6. concentrationconcentrated
  7. customThe residue was partitioned between ethyl acetate and water
  8. customThe organic phase was collected
  9. washwashed with brine
  10. dry with materialdried (anhydrous MgSO4)
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customThe resulting orange solid was triturated with ether

Quellen und Nachweise

ORD-Eintrag
ord-df937bfb38384629b1fa9fdfccbde3e6
Quelldatensatz
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08093264B2

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