تفاعل #306729

ord-df5084d69dc7417d97fb4768535dcf5d

معادلة التفاعل

O=C(Cl)c1cc2cc(Cl)cc(Cl)c2[nH]1
5,7-dichloro-indole-2-carbonylchloride
c1ccncc1
pyridine
Nc1ccc(S(=O)(=O)Nc2nccs2)cc1
N′-(2-thiazolyl)sulfanilamide
O=C(Nc1ccc(S(=O)(=O)Nc2nccs2)cc1)c1cc2cc(Cl)cc(Cl)c2[nH]1
5,7-Dichloro-1H-indol-2-carboxylic acid [4-(thiazol-2-ylsulfamoyl)-phenyl]-amide
المردود 90.0%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    ترشيحThe resulting solid was filtered
  2. 2
    غسيلwashed with DCM (3×5 mL)
  3. 3
    أخرىdried under vacuum overnight
  4. 4
    أخرىto provide the product (0.21 g; yield=90%) as a white-green solid

الإجراء التجريبي

To a solution of 5,7-dichloro-indole-2-carbonylchloride (186 mg, 0.75 mmol) in pyridine (0.8 mL, 1 mmol) and DCM (5.2 mL) was added N′-(2-thiazolyl)sulfanilamide (128 mg, 0.5 mmol) and the reaction mixture stirred at rt for 16 h. The resulting solid was filtered, washed with DCM (3×5 mL), and dried under vacuum overnight to provide the product (0.21 g; yield=90%) as a white-green solid. 1H-NMR (DMSO-d6) 12.78 (s, 1H), 12.33 (s, 1H), 10.67 (s, 1H), 7.97 (d, J=7.0 Hz, 2H), 7.82 (d, J=7.0 Hz, 2H), 7.62 (d, J=1.5 Hz, 1H), 7.47 (s, 1H), 7.30 (d, J=1.7 Hz, 1H), 7.27 (d, J=4.6 Hz, 1H), 6.84 (d, J=4.6 Hz, 1H). LC/MS (10-99%) M/Z: M+1 obs=467.0; tR=3.12 min.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08202861B2uspto-grants-2012_06