Tetramethyltin → 5-(5-chloro-benzo[1,3]dioxol-4-yl)-6-cyano-7-methyl-4-oxo-4,5-dihydro-3H-1-thia-3,5,8-triaza-acenaphthylene-2-carboxylic acid ethyl ester

HRID 32341

Reaktionsgleichung

[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]2[N:9]=[C:10](Cl)[C:11]([C:29]#[N:30])=[C:12]3[C:17]=2[C:16]=1[NH:15][C:14](=[O:18])[N:13]3[C:19]1[C:27]2[O:26][CH2:25][O:24][C:23]=2[CH:22]=[CH:21][C:20]=1[Cl:28])=[O:5])[CH3:2].[CH3:32][Sn](C)(C)C>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]2[N:9]=[C:10]([CH3:32])[C:11]([C:29]#[N:30])=[C:12]3[C:17]=2[C:16]=1[NH:15][C:14](=[O:18])[N:13]3[C:19]1[C:27]2[O:26][CH2:25][O:24][C:23]=2[CH:22]=[CH:21][C:20]=1[Cl:28])=[O:5])[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

7-chloro-5-(5-chloro-benzo[1,3]dioxol-4-yl)-6-cyano-4-oxo-4,5-dihydro-3H-1-thia-3,5,8-triaza-acenaphthylene-2-carboxylic acid ethyl ester Compound 1g (115 mg, 0.242 mmol) was combined with 95% tetramethyltin (0.039 ml, 0.266 mmol), PdCl2(Ph3P)2 (17 mg, 0.024 mmol) and DMF (3 mL) in a sealed microwave vessel. The mixture was heated to 150° C. for 15 mins. The reaction mixture was diluted with 0.5 M NaH2PO4 and extracted with EtOAc, then dried (MgSO4) and evaporated. The resulting residue was purified by flash chromatography (30 to 50% EtOAc/hexane/1% Et3N) to give 5-(5-chloro-benzo[1,3]dioxol-4-yl)-6-cyano-7-methyl-4-oxo-4,5-dihydro-3H-1-thia-3,5,8-triaza-acenaphthylene-2-carboxylic acid ethyl ester Compound 2a (57 mg) as a white solid. LC/MS 457 (MH+).

Aufarbeitung

extractionextracted with EtOAc
dry with materialdried (MgSO4)
customevaporated
customThe resulting residue was purified by flash chromatography (30 to 50% EtOAc/hexane/1% Et3N)

Quellen und Nachweise

ORD-Eintrag: ord-a8597d5ae96049e992fda0382df24d55
Quelldatensatz: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07427625B2

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