Tetrahydrofuran → (S)-1-(1-{[4-(3-fluorophenyl)-2-oxo-2H-chromen-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1-(trifluoromethyl)propyl 4-nitrobenzoate

HRID 2422485Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2422485
[N:1]([CH2:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)=[CH:10][C:11](=[O:15])[O:12]2)=[CH:7][CH:6]=1)=[N+:2]=[N-:3].[N+:23]([C:26]1[CH:43]=[CH:42][C:29]([C:30]([O:32][C:33]([CH2:40][CH3:41])([C:36]([F:39])([F:38])[F:37])[C:34]#[CH:35])=[O:31])=[CH:28][CH:27]=1)([O-:25])=[O:24].C1COCC1>C(OCC)(=O)C.[Cu](I)I>[N+:23]([C:26]1[CH:27]=[CH:28][C:29]([C:30]([O:32][C@@:33]([C:34]2[N:3]=[N:2][N:1]([CH2:4][C:5]3[CH:14]=[C:13]4[C:8]([C:9]([C:16]5[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=5)=[CH:10][C:11](=[O:15])[O:12]4)=[CH:7][CH:6]=3)[CH:35]=2)([C:36]([F:37])([F:38])[F:39])[CH2:40][CH3:41])=[O:31])=[CH:42][CH:43]=1)([O-:25])=[O:24]

Komponenten

6

Edukt 3

HCID 8028TetrahydrofuranHCID 597748703-(Trifluoromethyl)pent-1-YN-3-YL 4-nitrobenzoateHCID 597748747-(azidomethyl)-4-(3-fluorophenyl)-2H-chromen-2-one

Produkt 1

HCID 86621965(S)-1-(1-{[4-(3-fluorophenyl)-2-oxo-2H-chromen-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1-(trifluoromethyl)propyl 4-nitrobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 7-(azidomethyl)-4-(3-fluorophenyl)-2H-chromen-2-one (30 mg, 0.1 mmol) and 1-ethyl-1-(trifluoromethyl)prop-2-yn-1-yl 4-nitrobenzoate (S-isomer, the second, slower eluting enantiomer from step 2) (27 mg, 0.1 mmol) in THF (5 mL) N,N-diisopropylethylamine (79 uL, 0.45 mmol) and copper iodide (26 mg, 0.14 mmol) were added. After overnight stirring, the reaction was diluted with ethyl acetate, filtered and washed with water and brine. The organic layer was then dried over MgSO4, filtered and concentrated. The crude residue obtained was purified by column chromatography (acetone/CH2Cl2 5:95) to afford the title compound. 1H NMR (400 MHz, acetone-d6): 8.5 (s, 1H), 8.42 (d, 2H), 8.31 (d, 2H), 7.7-7.6 (m, 1H), 7.51 (d, 1H), 7.4-7.25 (m, 5H), 6.42 (s, 1H), 5.89 (s, 2H), 3.1-2.98 (m, 1H), 2.91-2.8 (m, 1H), 1.14 (t, 3H).

Aufarbeitung

  1. filtrationfiltered
  2. washwashed with water and brine
  3. dry with materialThe organic layer was then dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue obtained
  7. customwas purified by column chromatography (acetone/CH2Cl2 5:95)

Quellen und Nachweise

ORD-Eintrag
ord-e14cabe28a86496e80c40cfe2658bb63
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960409B2

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