تفاعل #41735

ord-af93c00e6e8647f084581f242bb9372d

معادلة التفاعل

Oc1ccc2oc(Nc3ccc(Br)cc3)nc2c1
2-[(4-bromophenyl)amino]benzoxazol-5-ol
C[Si](C)(C)[N-][Si](C)(C)C.[K+]
potassium bis(trimethylsilyl)amide
CNC(=O)c1cc(Cl)ccn1
4-chloro(2-pyridyl)-N-methylcarboxamide
O=C([O-])[O-].[K+].[K+]
Potassium carbonate
CNC(=O)c1cc(Oc2ccc3oc(Nc4ccc(Br)cc4)nc3c2)ccn1
desired product
CNC(=O)c1cc(Oc2ccc3oc(Nc4ccc(Br)cc4)nc3c2)ccn1
(4-{2-[(4-bromophenyl)amino]benzoxazol-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]benzoxazol-5-ol (1 eq), potassium bis(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+=439.

المصدر

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