Reaktion #676857

Reaktionsgleichung

5-bromo-3-methyl-benzothiophene-2-sulfonyl chloride

Intermediate 10

5-bromo-3-methyl-benzothiophene-2-sulfonyl chloride

ethyl 3-aminobenzoate

pyridine

→

title compound

Ausbeute 36.0%

Ethyl 3-{[(5-bromo-3-methyl-1-benzothiophen-2-yl)sulfonyl]amino}benzoate

Ausbeute 36.0%

Lösungsmittel

CH2Cl2

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with water and aqueous HCl
2. 2
   Sonstigedried
3. 3
   Einengenconcentrated
4. 4
   SonstigeThe residue was purified on silica

Vorschrift

A solution of 5-bromo-3-methyl-benzothiophene-2-sulfonyl chloride (Intermediate 10) (1.00 g, 3.26 mmol), ethyl 3-aminobenzoate (550 mg, 3.33.mmol) and pyridine (3 mL) in CH2Cl2 (150 mL) was stirred at room temperature overnight. The reaction was diluted with CH2Cl2, washed with water and aqueous HCl, dried and concentrated. The residue was purified on silica, using CH2Cl2 as eluent, resulting in 532 mg (36%) of the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 1.34 (t, J=7.09 Hz, 3 H) 2.44 (s, 3 H) 4.34 (q, J=7.09 Hz, 2 H) 6.85 (s, 1H) 7.36 (dd, J=8.03, 7.62 Hz, 1 H) 7.43 (ddd, J=8.03, 2.26, 1.25 Hz, 1 H) 7.57 (dd, J=8.66, 1.88 Hz, 1 H) 7.65 (dd, J=8.66, 0.50 Hz, 1 H) 7.72 (dd, J=2.26, 1.63 Hz, 1 H) 7.84 (ddd, J=7.62, 1.63, 1.25 Hz, 1 H) 7.87 (dd, J=1.88, 0.50 Hz, 1 H). MS (ESI+) m/z 454 [M+H]+.

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