4-Toluenesulfonyl chloride → 6-Fluoro-1-tosylindoline

HRID 56068

Reaktionsgleichung

Reaktionsgleichung von HRID 56068
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[F:12][C:13]1[CH:21]=[C:20]2[C:16]([CH2:17][CH2:18][NH:19]2)=[CH:15][CH:14]=1.[NH4+].[Cl-]>C1COCC1.N1C=CC=CC=1>[F:12][C:13]1[CH:21]=[C:20]2[C:16]([CH2:17][CH2:18][N:19]2[S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])=[CH:15][CH:14]=1

Komponenten

6

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 25517Ammonium ChlorideHCID 2604006-fluoro-2,3-dihydro-1H-indole

Produkt 1

HCID 606033976-Fluoro-1-tosylindolineAusbeute 61,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-Toluenesulfonyl chloride (460 mg, 2.4 mmol) was slowly added to a solution of 6-fluoro-2,3-dihydro-1H-indole (220 mg, 1.6 mmol) in THF (6 mL) and pyridine (260 μL). The reaction mixture was stirred at room temperature overnight. Upon the completion of the reaction, the mixture was cooled to 0° C., neutralized with aq. sat. NH4Cl (10 mL) and extracted with EtOAc (3×10 mL). The combined extracts were sequentially washed with aq. sat. NH4Cl (3×10 mL), brine (10 mL) and dried (MgSO4). The crude product was concentrated and dried over high vacuum. Chromatography of the residue (EtOAc/hexanes=1/3) gave 283 mg (0.98 mmol) of the title product. Yield: 61%, colorless oil. 1H NMR (300 MHz, CDCl3): δ 7.67 (d, J=8.2 Hz, 2H), 7.35 (dd, J=10.0, 2.3 Hz, 1H), 7.23 (d, J=8.2 Hz, 2H), 6.97 (m, 1H), 6.62 (m, 1H), 3.90 (t, J=8.4 Hz, 2H), 2.84 (t, J=8.4 Hz, 2H), 2.35 (s, 3H) ppm. 13C NMR (75 MHz, CDCl3): δ 162.5 (d, J=241.4 Hz), 144.5, 143.3 (d, J=11.7 Hz), 133.6, 129.8, 127.2, 127.0 (d, J=2.6 Hz), 125.7 (d, J=9.8 Hz), 110.0 (d, J=22.6 Hz), 102.8 (d, J=28.4 Hz), 50.7, 27.1, 21.5 ppm.

Aufarbeitung

  1. customUpon the completion of the reaction
  2. temperaturethe mixture was cooled to 0° C.
  3. extractionextracted with EtOAc (3×10 mL)
  4. washThe combined extracts were sequentially washed with aq. sat. NH4Cl (3×10 mL), brine (10 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationThe crude product was concentrated
  7. customdried over high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-3bbb81c43f5643c897226bdd9bb9b9fe
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434699B2

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