تفاعل #955925

ord-5b94722620b048ba997e2e6fe9baf93b

معادلة التفاعل

Br.BrCc1ccccn1
2-(bromomethyl)pyridine hydrobromide
Cc1ccc(-c2ccc(=S)[nH]n2)c(C)c1
6-(2,4-dimethylphenyl)pyridazine-3(2H)-thione
CC[O-].[Na+]
EtONa
Cc1ccc(-c2ccc(SCc3ccccn3)nn2)c(C)c1
3-(2,4-Dimethylphenyl)-6-(pyridin-2-ylmethylthio)pyridazine
المردود 35.0%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىthe reaction was irradiated in a microwave at 140° C. for 4 min
  2. 2
    تجفيفThe crude mixture was dried down
  3. 3
    أخرىpurified on silica gel (Eluent: 5% MeOH in DCM)

الإجراء التجريبي

To a mixture of 2-(bromomethyl)pyridine hydrobromide (116 mg; 0.46 mmol) and 6-(2,4-dimethylphenyl)pyridazine-3(2H)-thione (Example 13a) (100 mg, 0.46 mmol) in EtOH (3 mL) was added EtONa (20% in EtOH, 25 μl) and the reaction was irradiated in a microwave at 140° C. for 4 min. The crude mixture was dried down and purified on silica gel (Eluent: 5% MeOH in DCM) to give 3-(2,4-Dimethylphenyl)-6-(pyridin-2-ylmethylthio)pyridazine (49 mg, 35%) as a white solid. 1H NMR (300 MHz, dMSO: δ 2.49 (s, 3H), 2.54 (s, 3H), 4.09 (s, 2H), 6.32-6.37 (m, 2H), 6.45-6.52 (m, 2H), 6.75-6.78 (d, 1H), 6.84-6.87 (m, 2H), 6.95-6.98 (t, 1H), 7.67-7.68 (d,1H); MS (M+H, 308).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08968708B2uspto-grants-2015_03