Sodium Carbonate → HCID 68469291, Verbindung

HRID 1891391Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1891391
[Cl:1][C:2]1[C:7](B2OC(C)(C)C(C)(C)O2)=[CH:6][C:5]([S:17]([N:20]([CH3:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)(=[O:19])=[O:18])=[C:4]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][OH:33])[CH:3]=1.Br[C:35]1[C:40]([C:41]#[N:42])=[CH:39][C:38]([C:43]([F:46])([F:45])[F:44])=[N:37][CH:36]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[C:7]([C:35]2[CH:36]=[N:37][C:38]([C:43]([F:45])([F:46])[F:44])=[CH:39][C:40]=2[C:41]#[N:42])=[CH:6][C:5]([S:17]([N:20]([CH3:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)(=[O:19])=[O:18])=[C:4]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][OH:33])[CH:3]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 569733155-Bromo-2-(trifluoromethyl)isonicotinonitrileHCID 68471954HCID 68471954, Verbindung

Produkt 1

HCID 68469291HCID 68469291, VerbindungAusbeute 37,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 4-chloro-2-(4-hydroxy-butoxy)-N-methyl-N-pyridin-2-yl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzenesulfonamide (150 mg, 0.34 mmol), 5-bromo-2-trifluoromethyl-isonicotinonitrile (111 mg, 0.44 mmol), Pd(Ph3P)4 (40 mg, 0.034 mmol) and Na2CO3 (217 mg, 2.1 mmol) in dioxane (2 mL) and water (0.2 mL) was degassed with N2 for 5 min. The reaction vessel was sealed and then heated at 90° C. for 16 hrs. The mixture was absorbed onto silica gel and purified by chromatography on silica gel eluting with 20-25% acetone in hexanes to give 4-chloro-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-(4-hydroxy-butoxy)-N-methyl-N-pyridin-2-yl-benzenesulfonamide as an oil (69 mg). A small sample was also purified by prep. LCMS. MS: 541.1 (M+H)+; tR=7.59 min (method 2).

Aufarbeitung

  1. customwas degassed with N2 for 5 min
  2. customThe reaction vessel was sealed
  3. customThe mixture was absorbed onto silica gel
  4. custompurified by chromatography on silica gel eluting with 20-25% acetone in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-81d6025215d64d599d8c45f2558cc58a
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08507536B2

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