1-Acetylindoline-5-sulfonamide → 1-ethyl-2,3-dihydro-1H-indole-5-sulfonamide

HRID 528821Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 528821
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([S:13]([NH2:16])(=[O:15])=[O:14])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=O)[CH3:2].B.C1COCC1>C1COCC1>[CH2:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([S:13]([NH2:16])(=[O:14])=[O:15])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)[CH3:2]

Komponenten

4

Edukt 2

HCID 8042081-Acetylindoline-5-sulfonamide2×HCID 2723981Borane;tetrahydrofuran

Produkt 1

HCID 321037261-ethyl-2,3-dihydro-1H-indole-5-sulfonamideAusbeute 101,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of 1-acetylindoline-5-sulfonamide (Intermediate 52A, 120 mg, 0.50 mmol) in THF (2.0 mL) was added BH3.THF (5.0 mL, 5.0 mmol, 1.0M solution in THF). The resulting reaction mixture was stirred at room temperature for 1 h, then quenched carefully with MeOH and concentrated in vacuo to give the title compound (115 mg, 100%) as a white solid. 1H NMR (CD3OD) δ 7.56 (dd, J=8.4, 2.0 Hz, 1H), 7.48 (d, J=1.6 Hz, 1H), 6.46-6.44 (m, 1H), 3.51 (t, J=8.6 Hz, 2H), 3.24-3.20 (m, 2H), 2.99 (t, J=8.5 Hz, 2H), 1.17-1.13 (m, 3H); MS(ESI+) m/z 227.2 (M+H)+.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. customquenched carefully with MeOH
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a4461fd026ea40dfb4bae997112420eb
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346795B2

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