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Sodium hydride → Tert-butyl 4-(5-chloro-1-(3-fluoro-4-(methylsulfonyl)phenyl)-2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate

HRID 1962284
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1962284
[Cl:1][C:2]1[C:3]([O:9][CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[CH:4][C:5](=[O:8])[NH:6][CH:7]=1.[H-].[Na+].[F:25][C:26]1[CH:31]=[C:30](F)[CH:29]=[CH:28][C:27]=1[S:33]([CH3:36])(=[O:35])=[O:34]>CN(C=O)C>[Cl:1][C:2]1[C:3]([O:9][CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[CH:4][C:5](=[O:8])[N:6]([C:30]2[CH:29]=[CH:28][C:27]([S:33]([CH3:36])(=[O:34])=[O:35])=[C:26]([F:25])[CH:31]=2)[CH:7]=1
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Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 27583362,4-Difluoro-1-(methylsulfonyl)benzeneHCID 58467944Tert-butyl 4-(5-chloro-2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate

Produkt 1

HCID 58467945Tert-butyl 4-(5-chloro-1-(3-fluoro-4-(methylsulfonyl)phenyl)-2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylateAusbeute 52,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

A suspension of tert-butyl 4-(5-chloro-2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate (400 mg, 1.22 mmol), sodium hydride (60% wt in mineral oil, 58 mg, 1.5 mmol) and DMF (8 mL) was purged with Argon and then stirred at room temperature for 20 min. To the reaction was added 2,4-difluoro-1-(methylsulfonyl)benzene (351 mg, 1.83 mmol) and then heated at 130° C. for 1 hour. The resulting mixture was quenched with H2O and extracted with EtOAc. The organic layer was concentrated in vacuo to a brown oil. The oil was purified by flash chromatography (SiO2, 0 to 100% EtOAc in CH2Cl2) to yield 321 mg of the desired product as an off-white solid. 1H NMR (400 MHz, CDCl3) δ ppm 8.07-8.14 (m, 1H) 7.35-7.47 (m, 3H) 6.01 (s, 1H) 4.57-4.64 (m, 1H) 3.60-3.69 (m, 2H) 3.44-3.55 (m, 2H) 3.26 (s, 3H) 1.93-2.03 (m, 2H) 1.83-1.93 (m, 2H) 1.49 (s, 9H). MS (ESI) 445 (M−56+H).

Aufarbeitung

  1. customwas purged with Argon
  2. temperatureheated at 130° C. for 1 hour
  3. customThe resulting mixture was quenched with H2O
  4. extractionextracted with EtOAc
  5. concentrationThe organic layer was concentrated in vacuo to a brown oil
  6. customThe oil was purified by flash chromatography (SiO2, 0 to 100% EtOAc in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-d1f804a400ab486c9eaa7fdcba866487
Quelldatensatz
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08415367B2

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