Acetic Acid → HCID 58465881, Verbindung

HRID 455682Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 455682
CC(C)([O-])C.[K+].[NH2:7][C:8]1([CH2:24][OH:25])[C:21]2[CH:20]=[C:19]([Cl:22])[N:18]=[CH:17][C:16]=2[O:15][C:14]2[C:9]1=[CH:10][C:11]([Br:23])=[CH:12][CH:13]=2.[N+:26](/[CH:29]=[CH:30]/[CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)([O-:28])=[O:27].C(O)(=O)C>C1COCC1.[Cl-].[NH4+].O.CCOC(C)=O>[Br:23][C:11]1[CH:10]=[C:9]2[C:14](=[CH:13][CH:12]=1)[O:15][C:16]1[CH:17]=[N:18][C:19]([Cl:22])=[CH:20][C:21]=1[C:8]2([CH2:24][O:25][CH:30]([CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)[CH2:29][N+:26]([O-:28])=[O:27])[NH2:7]

Komponenten

9

Edukt 4

HCID 176Acetic AcidHCID 11094860132839-80-6HCID 23665647Potassium tert-butoxideHCID 58465926HCID 58465926, Verbindung2×

Produkt 1

HCID 58465881HCID 58465881, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

Potassium t-butoxide (0.517 g, 4.61 mmol) was added in one portion to a solution of (5-amino-7-bromo-3-chloro-5H-chromeno[2,3-c]pyridin-5-yl)methanol (Intermediate X, 1.5 g, 4.39 mmol) in THF (30 mL) at −78° C. After stirring for 45 minutes, (E)-(2-nitrovinyl)cyclohexane (0.716 g, 4.61 mmol) in THF (15.00 mL) was added slowly via syringe. The reaction was stirred at −78° C. for 20 minutes and was quenched with acetic acid (0.502 mL, 8.78 mmol) at −78° C., diluted with saturated aqueous ammonium chloride, water and EtOAc. After warming to RT, the layers were seperated and the aqueous layer was extracted with EtOAc. The combined organic extracts were washed with water, saturated aqueous sodium chloride, and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to give the crude material. The crude material was purified by silica gel chromatography by eluting with 1:6 to 1:4 EtOAc in hexane, to provide 7-bromo-3-chloro-5-((1-cyclohexyl-2-nitroethoxy)methyl)-5H-chromeno[2,3-c]pyridin-5-amine as a yellow oil. [M+H]+=496.1.

Aufarbeitung

  1. stirringThe reaction was stirred at −78° C. for 20 minutes
  2. customthe layers were seperated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. washThe combined organic extracts were washed with water, saturated aqueous sodium chloride
  5. dry with materialdried over sodium sulfate
  6. filtrationThe solution was filtered
  7. concentrationconcentrated in vacuo
  8. customto give the crude material
  9. customThe crude material was purified by silica gel chromatography
  10. washby eluting with 1:6 to 1:4 EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-5df1ee26405148ffbdd8bbb297e61310
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497264B2

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