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Dichloromethane → 3-[1-(4-Chloro-2-fluorophenyl)-1-cyclopropylethyl]-7-[(methylsulfinyl)methyl]-1H-indole

HRID 561593
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 561593
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:13]2[C:21]3[C:16](=[C:17]([CH2:22][S:23][CH3:24])[CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)([CH:10]2[CH2:12][CH2:11]2)[CH3:9])=[C:4]([F:25])[CH:3]=1.ClCCl.ClC1C=CC=C(C(OO)=[O:37])C=1>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:13]2[C:21]3[C:16](=[C:17]([CH2:22][S:23]([CH3:24])=[O:37])[CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)([CH:10]2[CH2:12][CH2:11]2)[CH3:9])=[C:4]([F:25])[CH:3]=1
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Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 583922333-[1-(4-Chloro-2-fluorophenyl)-1-cyclopropylethyl]-7-[(methylsulfanyl)methyl]-1H-indole

Produkt 1

HCID 583925433-[1-(4-Chloro-2-fluorophenyl)-1-cyclopropylethyl]-7-[(methylsulfinyl)methyl]-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887Methanol
Lösungsmittel

Versuchsvorschrift

100 mg (0.27 mmol) of the compound from Example 97 were introduced into 18 ml of dichloromethane at 0° C., 66 mg (0.27 mmol) of 70% pure meta-chloroperbenzoic acid were added, and the mixture was stirred at RT for 2 h. 2 ml of methanol were added, and the solvents were removed in vacuo. The residue was taken up in ethyl acetate and washed with water, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution. The solvents were removed in vacuo. The crude product was purified by preparative HPLC (mobile phase: acetonitrile/water gradient) to result in 86 mg (83% of theory) of the title compound as mixture of diastereomers.

Aufarbeitung

  1. customthe solvents were removed in vacuo
  2. washwashed with water, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  3. customThe solvents were removed in vacuo
  4. customThe crude product was purified by preparative HPLC (mobile phase: acetonitrile/water gradient)

Quellen und Nachweise

ORD-Eintrag
ord-bf0c8d552e664a1a924c7e2f22430b7a
Quelldatensatz
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08063234B2

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