تفاعل #41722

ord-b74b775937df4e8fb60155f9f1e1da68

معادلة التفاعل

Oc1ccc2sc(Nc3ccc(Br)cc3)nc2c1
2-[(4-bromophenyl)amino]benzothiazol-5-ol
C[Si](C)(C)[N-][Si](C)(C)C.[K+]
Potassiumbis(trimethylsilyl)amide
CNC(=O)c1cc(Cl)ccn1
4-chloro(2-pyridyl)-N-methylcarboxamide
O=C([O-])[O-].[K+].[K+]
Potassium carbonate
CNC(=O)c1cc(Oc2ccc3sc(Nc4ccc(Br)cc4)nc3c2)ccn1
desired product
CNC(=O)c1cc(Oc2ccc3sc(Nc4ccc(Br)cc4)nc3c2)ccn1
(4-{2-[(4-bromophenyl)amino]benzothiazol-5-yloxy}(2-pyridyl))-N-methylcarboxamide

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىmicrowaved for 6 mins at 150° C
  2. 2
    تركيزThe reaction mixture was then concentrated
  3. 3
    أخرىpartitioned between ethyl acetate and water
  4. 4
    أخرىThe organic layer was separated
  5. 5
    غسيلwashed with brine
  6. 6
    أخرىdried
  7. 7
    ترشيحfiltered
  8. 8
    تركيزconcentrated
  9. 9
    أخرىPurification on Prep LC

الإجراء التجريبي

The mixture containing 2-[(4-bromophenyl)amino]benzothiazol-5-ol (1 eq), Potassiumbis(trimethylsilyl)amide (4 eq), was stirred in dimethylformamide for 30 min at room temperature. To this mixture was added (4-chloro(2-pyridyl)-N-methylcarboxamide (1 eq) and Potassium carbonate (1.2 eq) and microwaved for 6 mins at 150° C. The reaction mixture was then concentrated and partitioned between ethyl acetate and water. The organic layer was separated and washed with brine, dried, filtered and concentrated. Purification on Prep LC yielded the desired product. MS: MH+=455

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07728010B2uspto-grants-2010_06