Sodium Bicarbonate → N-(5'-Bromo-4-(difluoromethyl)spiro[cyclohexane-1,2'-indene]-3'(1'H)-ylidene)-2-methylpropane-2-sulfinamide

HRID 1965148Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1965148
[CH3:1][C:2]([S:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[Br:8][C:9]1[CH:17]=[C:16]2[C:12]([CH2:13][C:14]3([CH2:23][CH2:22][CH:21]([CH:24]([F:26])[F:25])[CH2:20][CH2:19]3)[C:15]2=O)=[CH:11][CH:10]=1.C([O-])(O)=O.[Na+]>[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC.CCOC(C)=O>[Br:8][C:9]1[CH:17]=[C:16]2[C:12](=[CH:11][CH:10]=1)[CH2:13][C:14]1([CH2:23][CH2:22][CH:21]([CH:24]([F:25])[F:26])[CH2:20][CH2:19]1)[C:15]2=[N:7][S:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[O:6]

Komponenten

6

Edukt 3

HCID 516892Sodium BicarbonateHCID 3382465Tert-Butanesulfinamide2×HCID 679794786'-Bromo-4-(difluoromethyl)spiro[cyclohexane-1,2'-inden]-1'(3'H)-one2×

Produkt 1

HCID 67979575N-(5'-Bromo-4-(difluoromethyl)spiro[cyclohexane-1,2'-indene]-3'(1'H)-ylidene)-2-methylpropane-2-sulfinamideAusbeute 60,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 76524Titanium tetraethoxideKatalysator2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Titanium ethoxide (0.893 mL, 4.33 mmol), 2-methylpropane-2-sulfinamide (0.315 g, 2.60 mmol) and 6′-bromo-4-(difluoromethyl)spiro[cyclohexane-1,2′-inden]-1′(3′H)-one (Intermediate 91, 0.713 g, 2.17 mmol) were dissolved in 2-Me THF (5 mL) and heated to 90° C. overnight. 2-Methylpropane-2-sulfinamide (0.315 g, 2.60 mmol) and titanium ethoxide (0.893 mL, 4.33 mmol) were added and the reaction was refluxed for 7 h. Another portion of reagents was added and the mixture was refluxed overnight. The reaction was allowed to attain r.t. EtOAc (50 mL) was added followed by dropwise addition of NaHCO3 (10 mL). The mixture was stirred at r.t. for 2 h. The crude product was purified using flash chromatography (40 g SiO2, 0-40% EtOAc in heptane) to give the title compound (564 mg, 60% yield): MS (ES+) m/z 432 [M+H]+.

Aufarbeitung

  1. temperaturethe reaction was refluxed for 7 h
  2. additionAnother portion of reagents was added
  3. temperaturethe mixture was refluxed overnight
  4. customto attain r.t
  5. customThe crude product was purified

Quellen und Nachweise

ORD-Eintrag
ord-b396e8711b264ba0984af804e2fb33a6
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415483B2

Notizen zur Reaktion

Wird geladen…