Diisopropylethylamine → (S)-1-{1-[(2-cyano-4-phenylquinolin-7-yl)methyl]-1H-1,2,3-triazol-4-yl}-1-(trifluoromethyl)propyl 4-nitrobenzoate

HRID 2422529Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2422529
[N:1]([CH2:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:10][C:11]([C:15]#[N:16])=[N: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].C(N(C(C)C)CC)(C)C>C1COCC1.[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:17]5[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=5)=[CH:10][C:11]([C:15]#[N:16])=[N: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 81531DiisopropylethylamineHCID 59774860HCID 59774860, VerbindungHCID 597748703-(Trifluoromethyl)pent-1-YN-3-YL 4-nitrobenzoate

Produkt 1

HCID 66791323(S)-1-{1-[(2-cyano-4-phenylquinolin-7-yl)methyl]-1H-1,2,3-triazol-4-yl}-1-(trifluoromethyl)propyl 4-nitrobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 7-(azidomethyl)-4-phenylquinoline-2-carbonitrile (120 mg, 0.42 mmol) and 1-ethyl-1-(trifluoromethyl)prop-2-yn-1-yl 4-nitrobenzoate (139 mg, 0.46 mmol, slower eluting enantiomer described in Example 1, step 2) in THF (5 mL) was added diisopropylethylamine (0.37 mL, 2.1 mmol) followed by copper iodide (120 mg, 0.63 mmol). The reaction was stirred at room temperature overnight and quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. Purification on silica gel (eluting with EtOAc/hexanes, 4:6) gave the title compound. MS (+ESI): 587 (M+H)+.

Aufarbeitung

  1. customquenched with saturated aqueous NH4Cl
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification on silica gel (eluting with EtOAc/hexanes, 4:6)

Quellen und Nachweise

ORD-Eintrag
ord-69d7c1497e7c4c2bbbb19dad87716a83
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960409B2

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