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Potassium Phosphate, Tribasic → 3-(3-bromo-5-(trifluoromethyl)phenyl)-N-(2,4-dimethoxybenzyl)-1-methyl-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide

HRID 1524409
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1524409
[CH3:1][O:2][C:3]1[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:4]=1[CH2:5][N:6]([C:29]1[S:33][N:32]=[CH:31][N:30]=1)[S:7]([C:10]1[CH:18]=[C:17]2[C:13]([C:14](B3OC(C)(C)C(C)(C)O3)=[CH:15][N:16]2[CH3:19])=[CH:12][CH:11]=1)(=[O:9])=[O:8].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Br:48][C:49]1[CH:54]=[C:53]([C:55]([F:58])([F:57])[F:56])[CH:52]=[C:51](Br)[CH:50]=1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl.CN(C=O)C>[Br:48][C:49]1[CH:50]=[C:51]([C:14]2[C:13]3[C:17](=[CH:18][C:10]([S:7]([N:6]([CH2:5][C:4]4[CH:34]=[CH:35][C:36]([O:38][CH3:39])=[CH:37][C:3]=4[O:2][CH3:1])[C:29]4[S:33][N:32]=[CH:31][N:30]=4)(=[O:9])=[O:8])=[CH:11][CH:12]=3)[N:16]([CH3:19])[CH:15]=2)[CH:52]=[C:53]([C:55]([F:56])([F:57])[F:58])[CH:54]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 20634891,3-Dibromo-5-(trifluoromethyl)benzeneHCID 71259251N-(2,4-dimethoxybenzyl)-1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide

Produkt 1

HCID 903882113-(3-bromo-5-(trifluoromethyl)phenyl)-N-(2,4-dimethoxybenzyl)-1-methyl-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamideAusbeute 34,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418807HCID 178418807, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A vial was charged with N-(2,4-dimethoxybenzyl)-1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide (0.200 g, 0.351 mmol), potassium phosphate (0.260 g, 1.227 mmol), and PdCl2(dppf)-CH2Cl2 (0.029 g, 0.035 mmol). DMF (0.150 mL) was added, followed by 1,3-dibromo-5-(trifluoromethyl)benzene (0.166 ml, 1.052 mmol). The vial was flushed with argon, sealed, and stirred at 85° C. for two hours. The reaction was diluted with ethyl acetate and washed with water. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were washed with brine, dried with sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (silica gel, gradient elution 0 to 75% EtOAc:Hexane) to afford 3-(3-bromo-5-(trifluoromethyl)phenyl)-N-(2,4-dimethoxybenzyl)-1-methyl-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide (0.081 g, 0.121 mmol, 34.6% yield) as a white solid. m/z (ESI) 668.0 (M+H)+.

Aufarbeitung

  1. customThe vial was flushed with argon
  2. customsealed
  3. additionThe reaction was diluted with ethyl acetate
  4. washwashed with water
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. washthe combined organic layers were washed with brine
  7. dry with materialdried with sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe material was purified via column chromatography (silica gel, gradient elution 0 to 75% EtOAc:Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-a85f1d6b12b04964aa45c8c3ee559aa2
Quelldatensatz
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09079902B2

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