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Sodium Carbonate → N-(3.4-Dimethyl-5-isoxazolyl)-2'-formyl-4'-(2-pyrimidinyl) [1,1-biphenyl]-2-sulfonamide

HRID 1956965
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1956965
B([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:13]([C:20]1[O:24][N:23]=[C:22]([CH3:25])[C:21]=1[CH3:26])COCCOC)(=[O:12])=[O:11])(O)O.C(=O)([O-])[O-].[Na+].[Na+].Br[C:34]1[CH:41]=[CH:40][C:39]([C:42]2[N:47]=[CH:46][CH:45]=[CH:44][N:43]=2)=[CH:38][C:35]=1[CH:36]=[O:37]>C1(C)C=CC=CC=1.CCO.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:25][C:22]1[C:21]([CH3:26])=[C:20]([NH:13][S:10]([C:5]2[C:4]([C:34]3[CH:41]=[CH:40][C:39]([C:42]4[N:47]=[CH:46][CH:45]=[CH:44][N:43]=4)=[CH:38][C:35]=3[CH:36]=[O:37])=[CH:9][CH:8]=[CH:7][CH:6]=2)(=[O:11])=[O:12])[O:24][N:23]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 3

HCID 10340Sodium CarbonateHCID 107862242-borono-N-(3,4-dimethyl-5-isoxazolyl)-N-[(2-methoxyethoxy)methyl]benzenesulfonamideHCID 186631922-Bromo-5-(2-pyrimidinyl)benzaldehyde

Produkt 1

HCID 18663185N-(3.4-Dimethyl-5-isoxazolyl)-2'-formyl-4'-(2-pyrimidinyl) [1,1-biphenyl]-2-sulfonamideAusbeute 116,3 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11979704
Tetrakis(triphenylphosphine)palladium
Katalysator
HCID 702EthanolLösungsmittel
HCID 962WaterLösungsmittel
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 0.554 g (1.188 mmol) of 2-borono-N-(3,4-dimethyl-5-isoxazolyl)-N-[(2-methoxyethoxy)methyl]benzenesulfonamide (prepared as described in U.S. patent application Ser. No. 08/603,975, filed Feb.20, 1996 by Murugesan et al. (Attorney Docket No. HA662d)) and 0.0578 g (0.05 mmol) of tetrakis(triphenylphosphine)-palladium(0) in 20 mL of toluene under argon, 10 mL of 2M aqueous sodium carbonate was added followed by 0.25 g (0.95 mmol) of the title compound of Step E added in 10 mL of 95% EtOH. The mixture was refluxed for 2 hrs and then diluted with 100 mL of water and extracted with 3×50 mL of EtOAc. The combined organic extracts were washed once with 100 mL of brine and dried and evaporated. The residue was chromatographed on 100 mL of silica gel using Hexanes/EtOAc 1:1 to afford 0.48 g (80%) of the title compound of this step as a colorless gum.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 2 hrs
  2. extractionextracted with 3×50 mL of EtOAc
  3. washThe combined organic extracts were washed once with 100 mL of brine
  4. customdried
  5. customevaporated
  6. customThe residue was chromatographed on 100 mL of silica gel

Quellen und Nachweise

ORD-Eintrag
ord-0bd75b1ef4ed4203958c6bb7fe1546dc
Quelldatensatz
uspto-grants-1998_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05780473

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