Toluene → 4-[5-(1,1-Dioxidothiomorpholin-4-yl)-3-nitropyridin-2-yl]morpholine

HRID 1431261Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1431261
Cl[C:2]1[CH:3]=[C:4]([N+:14]([O-:16])=[O:15])[C:5]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.[NH:17]1[CH2:22][CH2:21][S:20](=[O:24])(=[O:23])[CH2:19][CH2:18]1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.CC(C)([O-])C.[Na+].C1(C)C=CC=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[O:23]=[S:20]1(=[O:24])[CH2:21][CH2:22][N:17]([C:2]2[CH:3]=[C:4]([N+:14]([O-:16])=[O:15])[C:5]([N:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)=[N:6][CH:7]=2)[CH2:18][CH2:19]1

Komponenten

7

Edukt 5

HCID 1140TolueneHCID 6484228Thiomorpholine 1,1-dioxideHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23676156Sodium t-butoxideHCID 596312064-(5-Chloro-3-nitropyridin-2-yl)morpholine

Produkt 1

HCID 596313874-[5-(1,1-Dioxidothiomorpholin-4-yl)-3-nitropyridin-2-yl]morpholine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysator

Versuchsvorschrift

A stirred solution of 4-(5-chloro-3-nitropyridin-2-yl)morpholine (500 mg, 2.05 mmol), thiomorpholine 1,1-dioxide (333 mg, 2.46 mmol), Pd2dba3 (94 mg, 0.10 mmol), X-Phos (98 mg, 0.20 mmol), sodium tert-butoxide (394 mg, 4.1 mmol) in toluene (19.7 mL, 184.7 mmol) was heated at reflux for 14 h. After this time the reaction was cooled to rt and partitioned between EtOAc (100 mL) and NaHCO3 (satd aq. solution, 50 mL). The separated organic layer was washed with brine (50 mL), dried over magnesium sulfate, filtered and evaporated in vacuo. Column chromatography (hexanes:EtOAc, 1:0 to 1:1) gave 4-[5-(1,1-dioxidothiomorpholin-4-yl)-3-nitropyridin-2-yl]morpholine.

Aufarbeitung

  1. temperatureat reflux for 14 h
  2. custompartitioned between EtOAc (100 mL) and NaHCO3 (satd aq. solution, 50 mL)
  3. washThe separated organic layer was washed with brine (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-845f7dfe42174b5dbd81a64dd0442b68
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08940724B2

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