Borane;tetrahydrofuran → HCID 59395056, Verbindung

HRID 1915508Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1915508
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](O)([C:12]([F:15])([F:14])[F:13])[C:7](=O)[NH:8]2)=[CH:4][CH:3]=1.B.C1COCC1>C1COCC1.CN(C=O)C>[F:15][C:12]([F:13])([F:14])[C:6]1[C:5]2[C:9](=[CH:10][C:2]([NH2:1])=[CH:3][CH:4]=2)[NH:8][CH:7]=1

Komponenten

5

Edukt 2

HCID 2723981Borane;tetrahydrofuranHCID 59395032HCID 59395032, Verbindung

Produkt 1

HCID 59395056HCID 59395056, VerbindungAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 6-amino-3-hydroxy-3-(trifluoromethyl)indolin-2-one (58 mg, 0.25 mmol) in THF (0.5 mL) at 0° C. was added BH3.THF complex (1 M in THF, 1 mL, 0.95 mmol) dropwise. The reaction mixture was stirred for 5 min at 0° C. then for 3 h at room temperature. The reaction mixture was quenched by adding very carefully 6M HCl (3.5 mL) until no more gas release was observed. The reaction mixture was then stirred at 80° C. for 2 h. The solvent was removed under reduce pressure and the solid residue obtained was dissolved in DMF (3 mL), filtered and purified by reverse phase HPLC (10-99% CH3CN/H2O) to provide 3-(trifluoromethyl)-1H-indol-6-amine (30 mg, 54%, TFA salt).

Aufarbeitung

  1. waitfor 3 h at room temperature
  2. customThe reaction mixture was quenched
  3. additionby adding very carefully 6M HCl (3.5 mL) until no more gas release
  4. stirringThe reaction mixture was then stirred at 80° C. for 2 h
  5. customThe solvent was removed
  6. customthe solid residue obtained
  7. filtrationfiltered
  8. custompurified by reverse phase HPLC (10-99% CH3CN/H2O)

Quellen und Nachweise

ORD-Eintrag
ord-d9b9272a9007430a80c1e8eb26ae6158
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08614327B2

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