5-Fluoro-2-methylindole → 4-(5-Fluoro-2-methyl-1H-indol-3-yl)-2H-benzo[e][1,2,3]thiadiazine 1,1-dioxide

HRID 750685Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 750685
[Al+3].[Cl-].[Cl-].[Cl-].Cl[C:6]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[S:9](=[O:17])(=[O:16])[NH:8][N:7]=1.[F:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][C:23]([CH3:28])=[CH:22]2>ClCCCl.O>[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:6]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[S:9](=[O:17])(=[O:16])[NH:8][N:7]=1

Komponenten

6

Edukt 3

HCID 27787155-Fluoro-2-methylindoleHCID 6451240Aluminum(III) ChlorideHCID 597538444-chloro-2H-1lambda6,2,3-benzothiadiazine-1,1-dione

Produkt 1

HCID 1363886124-(5-Fluoro-2-methyl-1H-indol-3-yl)-2H-benzo[e][1,2,3]thiadiazine 1,1-dioxideAusbeute 19,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

AlCl3 (1.2 g, 10.5 mmol) was added to a solution of 4-chloro-2H-benzo[e][1,2,3]thiadiazine 1,1-dioxide (1.5 g, 7.0 mmol) and 5-fluoro-2-methyl indole (1.0 g, 7.0 mmol) in DCE (35 mL), and stirred overnight at 70° C. The reaction solution was diluted with H2O, and the product was extracted with a solution of CH2Cl2/EtOH (9/1, v/v). The extracted product was concentrated and purified via silica gel chromatography eluting with a gradient of 0 to 70% EtOAc in hexanes to afford 0.44 g (19%) of the sub-title compound. MS calculated for C16H12FN3O2S—H: 328, observed: 328.

Aufarbeitung

  1. extractionthe product was extracted with a solution of CH2Cl2/EtOH (9/1
  2. concentrationThe extracted product was concentrated
  3. custompurified via silica gel chromatography
  4. washeluting with a gradient of 0 to 70% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-43356af550a8429bbb33bdc0cb6dbe39
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405215B2

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