Sodium methanethiolate → 4-(5-Bromo-6-chloro-pyridine-3-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester

HRID 2216034Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2216034
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([N+]([O-])=O)=[C:8]([S:10]([C:13]2[CH:14]=[N:15][C:16]([Cl:20])=[C:17]([Br:19])[CH:18]=2)(=[O:12])=[O:11])[CH:9]=1)=[O:4].[CH3:24][S-:25].[Na+]>>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([S:25][CH3:24])=[C:8]([S:10]([C:13]2[CH:14]=[N:15][C:16]([Cl:20])=[C:17]([Br:19])[CH:18]=2)(=[O:12])=[O:11])[CH:9]=1)=[O:4]

Komponenten

3

Edukt 2

HCID 4378561Sodium methanethiolateHCID 210571744-(5-Bromo-6-chloro-pyridine-3-sulfonyl)-5-nitro-thiophene-2-carboxylic acid methyl ester

Produkt 1

HCID 210571794-(5-Bromo-6-chloro-pyridine-3-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl esterAusbeute 21 %

Versuchsvorschrift

The procedure as in Example 27, a was followed using 4-(5-bromo-6-chloro-pyridine-3-sulfonyl)-5-nitro-thiophene-2-carboxylic acid methyl ester (3.5 g, 8.10 mmol, Example 118, step b) and sodium thiomethoxide (560 mg, 8.10 mmol as 1M solution in EtOH). The reaction was allowed to stir for 2.5 hours and was quenched with acetic acid. The resulting mixture was dissolved into EtOAc, and aqueous work up with brine and saturated NaHCO3 resulted in isolation of a mixture. This mixture was purified by SiO2 flash column chromatography (Biotage—40 M, 100% hexanes to 25% EtOAc in hexanes). The product was isolated as a yellow solid (750 mg, 21%). ESI-MS (m/z): Calcd. for C12H10BrClNO4S3: 441.8 (M+H); found: 442.1. 1H-NMR (CD3OD+CDCl3): δ 8.93 (m, 1H), 8.50 (m, 1H), 8.06 (s, 1H), 3.91 (m, 3H), 2.67 (m, 3H).

Aufarbeitung

  1. customwas quenched with acetic acid
  2. dissolutionThe resulting mixture was dissolved into EtOAc, and aqueous work up with brine and saturated NaHCO3
  3. customresulted in isolation of a mixture
  4. customThis mixture was purified by SiO2 flash column chromatography (Biotage—40 M, 100% hexanes to 25% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-10f150658b0544fa8b15b29350c2b2c6
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07109354B2

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