Chloroform → (R)-(3-(Dimethylamino)pyrrolidin-1-yl)(7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)methanone

HRID 2193658

Reaktionsgleichung

Reaktionsgleichung von HRID 2193658
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([N:13]3[CH2:17][CH2:16][C@@H:15]([N:18]([CH3:20])[CH3:19])[CH2:14]3)=[O:12])[S:10][C:3]=12.[F:21][C:22]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[CH:25]=[CH:24][C:23]=1[OH:31].C([O-])([O-])=O.[K+].[K+].C(Cl)(Cl)Cl>O(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:19][N:18]([CH3:20])[C@@H:15]1[CH2:16][CH2:17][N:13]([C:11]([C:9]2[S:10][C:3]3[C:4](=[N:5][CH:6]=[CH:7][C:2]=3[O:31][C:23]3[CH:24]=[CH:25][C:26]([N+:28]([O-:30])=[O:29])=[CH:27][C:22]=3[F:21])[CH:8]=2)=[O:12])[CH2:14]1

Komponenten

6

Edukt 4

HCID 6212ChloroformHCID 98252-Fluoro-4-nitrophenolHCID 11430Potassium CarbonateHCID 20745989(R)-(7-Chlorothieno[3,2-b]pyridin-2-yl)(3-(dimethylamino)pyrrolidin-1-yl)methanone

Produkt 1

HCID 58790264(R)-(3-(Dimethylamino)pyrrolidin-1-yl)(7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)methanoneAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7583Diphenyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
190 °C

Versuchsvorschrift

A mixture of the amide 24 (1.44 g, 4.65 mmol), 2-fluoro-4-nitrophenol (2.21 g, 14.1 mmol) and K2CO3 (2.56 g, 18.5 mmol) in Ph2O (5.0 mL) was heated at 190° C. for 3 hrs. CHCl3 (100 mL) was added to the resultant dark brown mixture and then the mixture was extracted with 1M HCl. The aqueous phase was washed with CHCl3 and basified with NH4OH (pH 11). The resultant cloudy mixture was extracted with CHCl3 and the organic phase was collected, washed with water, dried over anhydrous Na2SO4 then concentrated under reduced pressure. The remaining yellow solid material was purified by flash chromatography, eluent CHCl3/MeOH (95:5, then 80:20) to afford title compound 25 as a white solid (1.41 g, 3.28 mmol, 71% yield). MS (m/z): 431.0 (M+H).

Aufarbeitung

  1. extractionthe mixture was extracted with 1M HCl
  2. washThe aqueous phase was washed with CHCl3
  3. extractionThe resultant cloudy mixture was extracted with CHCl3
  4. customthe organic phase was collected
  5. washwashed with water
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationthen concentrated under reduced pressure
  8. customThe remaining yellow solid material was purified by flash chromatography, eluent CHCl3/MeOH (95:5

Quellen und Nachweise

ORD-Eintrag
ord-7316cc94d85642aa827ac05627c59721
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329726B2

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