StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Cesium carbonate → 5-(2-phenylpyrrolidin-1-yl)-N-(1,2,4-thiadiazol-5-yl)naphthalene-2-sulfonamide

HRID 1473345
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1473345
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([S:12]([N:15](CC1C=CC(OC)=CC=1OC)[C:16]1[S:20][N:19]=[CH:18][N:17]=1)(=[O:14])=[O:13])=[CH:7]2.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+].[C:80]1([CH:86]2[CH2:90][CH2:89][CH2:88][NH:87]2)[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O.CO.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].C1(C)C=CC=CC=1>[C:80]1([CH:86]2[CH2:90][CH2:89][CH2:88][N:87]2[C:2]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH:4]=[CH:5][C:6]([S:12]([NH:15][C:16]2[S:20][N:19]=[CH:18][N:17]=2)(=[O:14])=[O:13])=[CH:7]3)[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 4

HCID 10796Cesium carbonateHCID 2618922-PhenylpyrrolidineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 866873455-bromo-N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)naphthalene-2-sulfonamide

Produkt 1

HCID 866873955-(2-phenylpyrrolidin-1-yl)-N-(1,2,4-thiadiazol-5-yl)naphthalene-2-sulfonamide
Ausbeute 44,7 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A vial was charged with 5-bromo-N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)naphthalene-2-sulfonamide (205 mg, 0.394 mmol), Xantphos (45.6 mg, 0.079 mmol), Pd2(dba)3 (36.1 mg, 0.039 mmol), and cesium carbonate (257 mg, 0.788 mmol). The vial was flushed with Ar (g), then toluene (3939 μl) and 2-phenylpyrrolidine (81 μl, 0.551 mmol) were added in sequence. The vial was sealed and heated at 100° C. for 16 h. The reaction mixture was partitioned between EtOAc and water. The layers were separated, and the organic extract was washed with brine. The combined aq. layers were extracted with EtOAc, and the organic layers were combined. The combined solution was washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by chromatography on silica gel with 0 to 50% EtOAc/Heptane to give a clear oil. This material was dissolved in DCM (2 mL) and TFA (1 mL), and the resulting mixture was stirred for 2 h. The mixture was diluted with MeOH, then concentrated. The crude product was purified by chromatography on silica gel with 0 to 5% MeOH/DCM to give 5-(2-phenylpyrrolidin-1-yl)-N-(1,2,4-thiadiazol-5-yl)naphthalene-2-sulfonamide (76.7 mg, 0.176 mmol) as a light-yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm=8.55-8.46 (m, 2H), 8.34 (d, J=2.1 Hz, 1H), 7.78 (dd, J=2.1, 9.0 Hz, 1H), 7.63 (d, J=8.2 Hz, 1H), 7.43-7.33 (m, 3H), 7.22-7.16 (m, 2H), 7.12-7.06 (m, 2H), 4.82 (dd, J=6.3, 9.1 Hz, 1H), 4.19-4.12 (m, 1H), 3.03 (dt, J=4.5, 8.9 Hz, 1H), 2.47-2.40 (m, 1H), 2.14-2.10 (m, 1H), 2.00-1.79 (m, 2H). m/z (ESI) 437.2 (M+H)+.

Aufarbeitung

  1. customThe vial was flushed with Ar (g)
  2. customThe vial was sealed
  3. customThe reaction mixture was partitioned between EtOAc and water
  4. customThe layers were separated
  5. extractionthe organic extract
  6. washwas washed with brine
  7. extractionThe combined aq. layers were extracted with EtOAc
  8. washThe combined solution was washed with brine
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was purified by chromatography on silica gel with 0 to 50% EtOAc/Heptane
  13. customto give a clear oil
  14. concentrationconcentrated
  15. customThe crude product was purified by chromatography on silica gel with 0 to 5% MeOH/DCM

Quellen und Nachweise

ORD-Eintrag
ord-308c97f689c943b9871bb235b329b4c0
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09012443B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion