Diethyl Ether → 5-((4-Chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)indolin-2-one

HRID 18125Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 18125
[F:1][C:2]([F:12])([F:11])[C:3]1[C:4]([Cl:10])=[N:5][C:6](Cl)=[N:7][CH:8]=1.CCOCC.[NH2:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][C:23](=[O:28])[CH2:22]2.C(N(CC)CC)C>[Cl-].[Zn+2].[Cl-].ClCCCl.CC(O)(C)C>[Cl:10][C:4]1[C:3]([C:2]([F:12])([F:11])[F:1])=[CH:8][N:7]=[C:6]([NH:18][C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[NH:24][C:23](=[O:28])[CH2:22]3)[N:5]=1

Komponenten

7

Edukt 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 27732135-Amino-2-oxindoleHCID 27827742,4-Dichloro-5-(trifluoromethyl)pyrimidine

Produkt 1

HCID 219231045-((4-Chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)indolin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 21868497Tert-butyl alcohol 1,2-dichloroethaneLösungsmittel

Versuchsvorschrift

To a solution of 5-trifluoromethyl-2,4-dichloropyrimidine (214.8 g; 0.921 mol) in 1:1 DCE/tBuOH (1.240 L) was added Zinc chloride 1M solution in ether (1 eq; 0.921 L). After 0.5 hour, 5-amino-oxindole (124 g; 0.837 mol) was added followed by triethylamine (129.4 ml; 0.921 mol) keeping temperature at 25° C. The reaction was allowed to stir at room temperature overnight, then was concentrated and the product triturated from methanol as a yellow solid (224.3 g; 82%). 1H NMR (DMSO-d6, 400 MHz) 3.29 (s, 2H), 6.76 (d, J=7.9 Hz, 2H), 7.39 (d, J=8.3 Hz), 7.51 (br s, 1H), 8.71 (s, 1H), 10.33 (s, 1H), 10.49 (s, 1H). 13C NMR (DMSO-d6, 100 MHz) δ 177.0, 161.3, 158.7 (br), 140.7, 132.8, 126.9, 123.7 (q, J=268 Hz), 121.0, 118.7, 111.2 (q, J=32 Hz), 109.6, 36.7; HPLC ret. time: 5.759 min. LRMS (M+) 329.1, 331.1.

Aufarbeitung

  1. customat 25° C
  2. concentrationwas concentrated
  3. customthe product triturated from methanol as a yellow solid (224.3 g; 82%)

Quellen und Nachweise

ORD-Eintrag
ord-31f12368ebb64b7d97c158f30cacfd86
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741336B2

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