Sodium Hydroxide → (6-Chloro-pyrimidin-4-yl)-(5-fluoro-2,3-dihydro-indol-1-yl)-methanone

HRID 74603

Reaktionsgleichung

Reaktionsgleichung von HRID 74603
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8](Cl)=[O:9])[CH:3]=1.[F:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][CH2:16][CH2:15]2.[OH-].[Na+].C(=O)([O-])O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([N:17]2[C:18]3[C:14](=[CH:13][C:12]([F:11])=[CH:20][CH:19]=3)[CH2:15][CH2:16]2)=[O:9])[CH:3]=1

Komponenten

6

Edukt 4

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 27744635-FluoroindolineHCID 184220986-Chloropyrimidine-4-carbonyl chloride

Produkt 1

HCID 58117506(6-Chloro-pyrimidin-4-yl)-(5-fluoro-2,3-dihydro-indol-1-yl)-methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

0.92 g (4.9 mmol) 6-chloro-pyrimidine-4-carboxylic acid chloride in 40 mL DCM were cooled in a bath of ice/acetone and mixed with 0.67 g (4.9 mmol) 5-fluoro-2,3-dihydro-1H-indole. Then 5.0 mL (5.0 mmol) of a 1N aqueous sodium hydroxide solution were added dropwise and the mixture was stirred for 1 h with cooling. 50 mL of a saturated sodium hydrogen carbonate solution were added and the mixture was stirred for a further 10 min. The organic phase was separated off, extracted with a 1N aqueous hydrochloric acid solution and with water, dried and evaporated down.

Aufarbeitung

  1. temperaturewith cooling
  2. stirringthe mixture was stirred for a further 10 min
  3. customThe organic phase was separated off
  4. extractionextracted with a 1N aqueous hydrochloric acid solution and with water
  5. customdried
  6. customevaporated down

Quellen und Nachweise

ORD-Eintrag
ord-f80c42c1602144118c73f0789d62eec9
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829006B2

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