Trifluoroacetic acid → 3-[1-Cyclopropyl-1-(4-methylphenyl)ethyl]-7-[(methylsulfanyl)methyl]-1H-indole

HRID 561633

Reaktionsgleichung

Reaktionsgleichung von HRID 561633
FC(F)(F)C(O)=O.[CH3:8][S:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:19]=1[NH:18][CH:17]=[CH:16]2.[CH:20]1([C:23]([C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)(O)[CH3:24])[CH2:22][CH2:21]1>ClCCl>[CH:20]1([C:23]([C:16]2[C:15]3[C:19](=[C:11]([CH2:10][S:9][CH3:8])[CH:12]=[CH:13][CH:14]=3)[NH:18][CH:17]=2)([C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)[CH3:24])[CH2:22][CH2:21]1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 98258alpha-Cyclopropyl-alpha,4-dimethylbenzenemethanolHCID 583921877-[(Methylsulfanyl)methyl]-1H-indole

Produkt 1

HCID 583922803-[1-Cyclopropyl-1-(4-methylphenyl)ethyl]-7-[(methylsulfanyl)methyl]-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

0.23 ml (3.00 mmol) of trifluoroacetic acid was added to 885 mg (4.99 mmol) of the compound from Example 8A and 440 mg (2.50 mmol) of the compound from Example 137A in 44 ml of dichloromethane, and the mixture was stirred at RT overnight. The reaction mixture was concentrated in a rotary evaporator. The residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 87.4 mg (10% of theory) of the title compound as mixture of diastereomers.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in a rotary evaporator
  2. customThe residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)

Quellen und Nachweise

ORD-Eintrag
ord-4da1d5476b2e4fe384010306eb100e3c
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063234B2

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