Lithium Chloride → (S)-1-(1-{[2-cyano-4-(1-ethoxyvinyl)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1-(trifluoromethyl)propyl 4-nitrobenzoate

HRID 2422539Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2422539
[N+:1]([C:4]1[CH:38]=[CH:37][C:7]([C:8]([O:10][C@@:11]([C:18]2[N:19]=[N:20][N:21]([CH2:23][C:24]3[CH:33]=[C:32]4[C:27]([C:28](Cl)=[CH:29][C:30]([C:34]#[N:35])=[N:31]4)=[CH:26][CH:25]=3)[CH:22]=2)([C:14]([F:17])([F:16])[F:15])[CH2:12][CH3:13])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].C([Sn](CCCC)(CCCC)[C:44]([O:46][CH2:47][CH3:48])=[CH2:45])CCC.[Cl-].[Li+]>O1CCOCC1.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N+:1]([C:4]1[CH:38]=[CH:37][C:7]([C:8]([O:10][C@@:11]([C:18]2[N:19]=[N:20][N:21]([CH2:23][C:24]3[CH:33]=[C:32]4[C:27]([C:28]([C:44]([O:46][CH2:47][CH3:48])=[CH2:45])=[CH:29][C:30]([C:34]#[N:35])=[N:31]4)=[CH:26][CH:25]=3)[CH:22]=2)([C:14]([F:17])([F:16])[F:15])[CH2:12][CH3:13])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Komponenten

7

Edukt 3

HCID 433294Lithium ChlorideHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 66790930(S)-1-{1-[(4-chloro-2-cyanoquinolin-7-yl)methyl]-1H-1,2,3-triazol-4-yl}-1-(trifluoromethyl)propyl 4-nitrobenzoate

Produkt 1

HCID 66791347(S)-1-(1-{[2-cyano-4-(1-ethoxyvinyl)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1-(trifluoromethyl)propyl 4-nitrobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of (S)-1-{1-[(4-chloro-2-cyanoquinolin-7-yl)methyl]-1H-1,2,3-triazol-4-yl}-1-(trifluoromethyl)propyl 4-nitrobenzoate (900 mg, 1.65 mmol), tributyl (1-ethoxyvinyl)tin (0.6 ml, 1.73 mmol) in dioxane (6 mL) was added lithium chloride (210 mg, 4.96 mmol) and Pd(PPh3)4 (95 mg, 0.083 mmol). The reaction mixture was stirred at 100° C. overnight then cooled to room temperature. The solution was then diluted with ethyl acetate, washed with sat. sol. of ammonium chloride, brine and dried over magnesium sulfate. The crude material was purified on silica gel (eluting solvent: 3% acetone in CH2Cl2) to afford the title compound. 1H NMR (400 MHz, acetone-d6): δ 8.52 (s, 1H), 8.42 (d, 2H), 8.39 (d, 1H), 8.30 (d, 2H), 8.05 (d, 1H), 7.95 (s, 1H), 7.75 (dd, 1H), 6.02 (s, 2H), 4.75 (dd, 2H), 4.12 (q, 2H), 3.05 (m, 1H), 2.85 (m, 1H), 1.40 (t, 3H), 1.15 (t, 3H).

Aufarbeitung

  1. temperaturethen cooled to room temperature
  2. washwashed with sat. sol. of ammonium chloride, brine
  3. dry with materialdried over magnesium sulfate
  4. customThe crude material was purified on silica gel (eluting solvent: 3% acetone in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-edc1cb95699d428fa2721af814571d51
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960409B2

Notizen zur Reaktion

Wird geladen…