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Sodium Carbonate → 4-(5-fluoro-2-methoxyphenyl)-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 527992
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 527992
Br[C:2]1[C:3]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:4]=2[N:5]=[CH:6][N:7]=1.COCCOC.C(O)C.C(=O)([O-])[O-].[Na+].[Na+].[F:35][C:36]1[CH:37]=[CH:38][C:39]([O:45][CH3:46])=[C:40](B(O)O)[CH:41]=1>C(OCC)(=O)C>[F:35][C:36]1[CH:41]=[CH:40][C:39]([O:45][CH3:46])=[C:38]([C:2]2[C:3]3[CH:10]=[CH:9][N:8]([S:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)(=[O:13])=[O:12])[C:4]=3[N:5]=[CH:6][N:7]=2)[CH:37]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 10340Sodium CarbonateHCID 27826735-Fluoro-2-methoxyphenylboronic acidHCID 20074477Dimethoxyethane ethanolHCID 904185894-bromo-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine

Produkt 1

HCID 904188734-(5-fluoro-2-methoxyphenyl)-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a suspension of Example 3A (5 g, 14.79 mmol) in 2:1 1,2-dimethyoxyethane/ethanol (150 mL) was added 2M aqueous sodium carbonate (29.6 mL, 59.1 mmol), (5-fluoro-2-methoxyphenyl)boronic acid (3.02 g, 17.74 mmol) and dichlorobis(triphenylphosphine) palladium(II) (1.038 g, 1.479 mmol). The mixture was heated at 100° C. for 1.5 hours, cooled and diluted with 100 mL ethyl acetate. The organic layer was washed with saturated sodium bicarbonate solution, water, and brine, dried over magnesium sulfate, filtered, and concentrated. The residue was triturated with dichloromethane, filtered, and dried under vacuum. The filtrate was concentrated to ⅓ volume, and the solid filtered and rinsed with dichloromethane. The remainder of the filtrate was purified by flash chromatography on silica (Analogix 280) eluting with a gradient of 15 to 70% ethyl acetate/hexane. This was combined with the triturated material and dried over vacuum to give the title compound. MS (ESI+) m/z 383.5 (M+H)+.

Aufarbeitung

  1. temperaturecooled
  2. washThe organic layer was washed with saturated sodium bicarbonate solution, water, and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was triturated with dichloromethane
  7. filtrationfiltered
  8. customdried under vacuum
  9. concentrationThe filtrate was concentrated
  10. filtrationthe solid filtered
  11. washrinsed with dichloromethane
  12. customThe remainder of the filtrate was purified by flash chromatography on silica (Analogix 280)
  13. washeluting with a gradient of 15 to 70% ethyl acetate/hexane
  14. customdried over vacuum

Quellen und Nachweise

ORD-Eintrag
ord-1eb5ce0404304813bd9c8a960f678188
Quelldatensatz
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09346813B2

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