4-t-Butylbenzenesulfonyl chloride → Methyl 3-(4-tert-butylphenylsulfonamido)thieno[2,3-b]pyridine-2-carboxylate

HRID 1925727

Reaktionsgleichung

Reaktionsgleichung von HRID 1925727
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[S:4][C:3]=1[C:11]([O:13][CH2:14]C)=[O:12].[C:16]([C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17]>N1C=CC=CC=1.O>[C:16]([C:20]1[CH:25]=[CH:24][C:23]([S:26]([NH:1][C:2]2[C:10]3[C:5](=[N:6][CH:7]=[CH:8][CH:9]=3)[S:4][C:3]=2[C:11]([O:13][CH3:14])=[O:12])(=[O:28])=[O:27])=[CH:22][CH:21]=1)([CH3:19])([CH3:17])[CH3:18]

Komponenten

5

Edukt 2

HCID 1398824-t-Butylbenzenesulfonyl chlorideHCID 738459Ethyl 3-aminothieno[2,3-b]pyridine-2-carboxylate

Produkt 1

HCID 59180440Methyl 3-(4-tert-butylphenylsulfonamido)thieno[2,3-b]pyridine-2-carboxylateAusbeute 12,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a solution of ethyl 3-aminothieno[2,3-b]pyridine-2-carboxylate (0.3 g; 1.35 mmol) in pyridine (10 mL) was added 4-tert-butylbenzenesulfonyl chloride (0.48 g; 2.03 mol). The reaction was stirred at room temperature for 18 hours and then diluted with water and extracted with ethyl acetate. The organic layer was separated and successively washed with aqueous hydrochloric acid (2N) and aqueous saturated sodium chloride solution, dried over magnesium sulfate, filtered, and evaporated under reduced pressure. The crude residue was purified by silica gel chromatography eluting with hexanes/ethyl acetate to yield the title compound as a white solid (0.070 g).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was separated
  3. washsuccessively washed with aqueous hydrochloric acid (2N) and aqueous saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe crude residue was purified by silica gel chromatography
  8. washeluting with hexanes/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-a4869878b4d840e09171b5f06e6b4f2c
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178699B2

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