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Sodium Hydroxide → HCID 66775751, Verbindung

HRID 1644848
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1644848
[CH2:1]([C:5]1[S:9][C:8]([S:10]([NH:13][C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:12])=[O:11])=[C:7](B(O)O)[CH:6]=1)[CH:2]([CH3:4])[CH3:3].Br[C:22]1[CH:33]=[CH:32][C:25]([CH2:26][N:27]2[CH:31]=[N:30][CH:29]=[N:28]2)=[CH:24][CH:23]=1.[OH-].[Na+]>C1(C)C=CC=CC=1.C(O)C.CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N:27]1([CH2:26][C:25]2[CH:24]=[CH:23][C:22]([C:7]3[CH:6]=[C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[S:9][C:8]=3[S:10]([NH:13][C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:12])=[O:11])=[CH:33][CH:32]=2)[CH:31]=[N:30][CH:29]=[N:28]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 14798Sodium HydroxideHCID 11484000(2-(N-(tert-Butyl)sulfamoyl)-5-isobutylthiophen-3-yl)boronic acidHCID 19043019HCID 19043019, Verbindung

Produkt 1

HCID 66775751HCID 66775751, VerbindungAusbeute 66,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11776TriphenylphosphineKatalysator
HCID 167845palladium(II) acetateKatalysator
HCID 21863594Toluene ethanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

5-iso-Butyl-2-(N-tert-butylaminosulfonyl)thiophene-3-boronic acid (0.479 g, 1.5 mmol, see Example 1(c) above), 1-(4-bromobenzyl)-1H-[1,2,4]triazole (0.238 g, 1 mmol, see step (a) above), Pd(OAc)2 (15.7 mg, 0.03 mmol), triphenyl phosphine (15.7 mg, 0.06 mmol) and NaOH (0.16 g, 4 mmol) were dissolved in 4 mL of toluene/ethanol (4:1) in a thick walled glass tube, and were then heated to 80° C. for 1 h. The reaction mixture was cooled to rt, extracted with ethyl acetate and water and subsequently dried over K2CO3. The solvent was evaporated and the reaction mixture was separated on a silica column (dichloromethane+1% methanol to dichloromethane+4% methanol) to yield 0.288 g of the sub-title compound (65% yield).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to rt
  2. extractionextracted with ethyl acetate and water
  3. dry with materialsubsequently dried over K2CO3
  4. customThe solvent was evaporated
  5. customthe reaction mixture was separated on a silica column (dichloromethane+1% methanol to dichloromethane+4% methanol)

Quellen und Nachweise

ORD-Eintrag
ord-cba9a1596d27426a9525a18b2923a596
Quelldatensatz
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08124638B2

Notizen zur Reaktion

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