Potassium Carbonate → (3-{2-[2-(4-Chloro-phenoxy)-ethyl]-1,1-dioxo-1,2-dihydro-1lambda6-benzo[e][1,2,3]thiadiazin-4-yl}-5-fluoro-2-methyl-indol-1-yl)-acetic acid tert-butyl ester

HRID 1819656

Reaktionsgleichung

Reaktionsgleichung von HRID 1819656
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1.C([O-])([O-])=O.[K+].[K+].[F:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][C:23]([CH3:28])=[C:22]2[C:29]1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[S:32](=[O:40])(=[O:39])[NH:31][N:30]=1.Br[CH2:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44]>CC#N.O.C(Cl)Cl>[C:46]([O:45][C:43](=[O:44])[CH2:42][N:24]1[C:25]2[C:21](=[CH:20][C:19]([F:18])=[CH:27][CH:26]=2)[C:22]([C:29]2[C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=3[S:32](=[O:39])(=[O:40])[N:31]([CH2:2][CH2:3][O:4][C:5]3[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=3)[N:30]=2)=[C:23]1[CH3:28])([CH3:49])([CH3:48])[CH3:47]

Komponenten

8

Edukt 4

HCID 11430Potassium Carbonate2×HCID 748541-(2-Bromoethoxy)-4-chlorobenzeneHCID 79177tert-Butyl bromoacetateHCID 1363886124-(5-Fluoro-2-methyl-1H-indol-3-yl)-2H-benzo[e][1,2,3]thiadiazine 1,1-dioxide

Produkt 1

HCID 67316049(3-{2-[2-(4-Chloro-phenoxy)-ethyl]-1,1-dioxo-1,2-dihydro-1lambda6-benzo[e][1,2,3]thiadiazin-4-yl}-5-fluoro-2-methyl-indol-1-yl)-acetic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

4-Chlorophenyl 2-bromoethyl ether (16 mg, 67 μmol) and K2CO3 (10 mg, 72 μmol) were added to a solution of 4-(5-fluoro-2-methyl-1H-indol-3-yl)-2H-benzo[e][1,2,3]thiadiazine 1,1-dioxide (20 mg, 61 μmol) in CH3CN (1 mL), and stirred overnight at 80° C. An additional amount of K2CO3 (10 mg, 72 μmol) and tert-butyl bromoacetate (14 μL, 92 μmol) was added, and the reaction mixture stirred an additional 2 h at 80° C. The reaction mixture was diluted with H2O and CH2Cl2, and filtered through an Extrelut column. The Extrelut column was washed with CH2Cl2, and the filtrate was concentrated to afford the sub-title compound, which was carried onto the next step without further purification or characterization.

Aufarbeitung

  1. stirringthe reaction mixture stirred an additional 2 h at 80° C
  2. filtrationfiltered through an Extrelut column
  3. washThe Extrelut column was washed with CH2Cl2
  4. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-48909f23694549fea34116431fc88e04
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07601749B2

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