(4-Methanesulfonamidophenyl)boronic acid → HCID 66930808, Verbindung

HRID 1364130Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1364130
[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9](B(O)O)=[CH:8][CH:7]=1)(=[O:4])=[O:3].[N:15]1[NH:16][CH:17]=[C:18]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20][C:19]=12>ClCCl.CO.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([N:16]2[CH:17]=[C:18]3[C:19]([CH2:20][CH2:21][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:23][CH2:24]3)=[N:15]2)=[CH:8][CH:7]=1)(=[O:4])=[O:3]

Komponenten

6

Edukt 2

HCID 2773537(4-Methanesulfonamidophenyl)boronic acidHCID 178451637HCID 178451637, Verbindung

Produkt 1

HCID 66930808HCID 66930808, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8895Cupric acetateKatalysatorHCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To {4-[(methylsulfonyl)amino]phenyl}boronic acid (commercially available from e.g. Combi-Blocks) (127 mg, 0.29 mmol) in dichloromethane (3 ml) was added copper(II) acetate (107 mg, 0.59 mmol) and 4 Å molecular sieves (190 mg), and the reaction stirred at room temperature, open to air, for 10 minutes. 1,1-Dimethylethyl 4,5,7,8-tetrahydropyrazolo[3,4-d]azepine-6(2H)-carboxylate (may be prepared as described in Description 9) (70 mg, 0.29 mmol) was added and the reaction stirred at room temperature, open to air, overnight. The reaction mixture was diluted with methanol and filtered through a celite pad, washing with methanol. Solvent was evaporated in vacuo. Ethyl acetate and water were added, and the product was extracted into ethyl acetate (×3), washed with water (×1), then saturated sodium bicarbonate solution (×1), and then dried over magnesium sulfate. Solvent was evaporated in vacuo. The resulting crude product was purified by column chromatography on silica gel, eluting with a mixture of ethyl acetate in hexane (0-50%). Relevant fractions were combined and solvent evaporated in vacuo. The resulting crude product was purified further by Mass Directed Autopreparation to afford the title compound (D39). MS (ES+) m/e 407 [M+H]+.

Aufarbeitung

  1. stirringthe reaction stirred at room temperature, open to air, overnight
  2. filtrationfiltered through a celite pad
  3. washwashing with methanol
  4. customSolvent was evaporated in vacuo
  5. additionEthyl acetate and water were added
  6. extractionthe product was extracted into ethyl acetate (×3)
  7. washwashed with water (×1)
  8. dry with materialsaturated sodium bicarbonate solution (×1), and then dried over magnesium sulfate
  9. customSolvent was evaporated in vacuo
  10. customThe resulting crude product was purified by column chromatography on silica gel
  11. washeluting with a mixture of ethyl acetate in hexane (0-50%)
  12. customsolvent evaporated in vacuo
  13. customThe resulting crude product was purified further by Mass Directed Autopreparation

Quellen und Nachweise

ORD-Eintrag
ord-a641d15199a14ea89a89395709d5d41d
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07888347B2

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