تفاعل #84059

ord-38d7ba10dbea4a1dae25d68ff5ee7f66

معادلة التفاعل

COc1ccc2nc(-c3ccc(-c4nnn[nH]4)cc3)c(C)cc2c1
2-(4-(1H-tetrazol-5-yl)phenyl)-6-methoxy-3-methylquinoline
Cc1cc2cc(O)ccc2nc1-c1ccc(-c2nnn[nH]2)cc1
Compound 2
المردود 38.1%
Cc1cc2cc(O)ccc2nc1-c1ccc(-c2nnn[nH]2)cc1
2-(4-(1H-tetrazol-5-yl)phenyl)-3-methylquinolin-6-ol
المردود 38.1%

الكواشف

لا شيء

المذيبات

ظروف التفاعل

درجة الحرارة
140°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    تركيزAfter concentration in vacuo the crude
  2. 2
    workup.DISSOLUTIONwas dissolved in 5 mL of 1N NaOH
  3. 3
    ترشيحThe solids were filtered
  4. 4
    أخرىdried in vacuo

الإجراء التجريبي

2-(4-(1H-tetrazol-5-yl)phenyl)-6-methoxy-3-methylquinoline (128 mg, 0.40 mmol) was dissolved in 5 mL of NMP and Na2S (47 mg, 0.60 mmol) was added to it. The mixture was then stirred for 4 hours at 140° C. in a microwave reactor. After concentration in vacuo the crude was dissolved in 5 mL of 1N NaOH and slowly acidified with 1N HCl to a pH of 4. The solids were filtered and dried in vacuo to afford 46.2 mg (38% yield) of Compound 2. 1H NMR (DMSO-d6, 400 MHz): δ 10.10-10.00 (bs, 1H), 8.18-8.15 (d, 2H), 8.08 (s, 1H), 7.87-7.84 (m, 3H), 7.30-7.26 (d, 1H), 7.13 (s, 1H), 2.45 (s, 3H). MS (ESI): m/z 304.11 [M+H]+.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US09433618B2uspto-grants-2016_09