تفاعل #169847

ord-e7b8ca838475418c88e53e5d7ee8864d

معادلة التفاعل

O
water
Nc1ccc(OCc2ccccc2)cc1
4-(benzyloxy)aniline
CCN(C(C)C)C(C)C
DIEA
COC(=O)c1c(C(F)(F)F)ccnc1F
methyl 2-fluoro-4-(trifluoromethyl)pyridine-3-carboxylate
COC(=O)c1c(C(F)(F)F)ccnc1Nc1ccc(OCc2ccccc2)cc1
title compound
المردود 11.0%
COC(=O)c1c(C(F)(F)F)ccnc1Nc1ccc(OCc2ccccc2)cc1
methyl 2-{[4-(benzyloxy)phenyl]amino}-4-(trifluoromethyl)pyridine-3-carboxylate
المردود 11.0%

المذيبات

ظروف التفاعل

درجة الحرارة
200°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    استخلاصthe mixture was extracted with EtOAc
  2. 2
    أخرىThe organic layer was separated
  3. 3
    غسيلwashed with water and brine
  4. 4
    تجفيفdried over Na2SO4
  5. 5
    تركيزconcentrated in vacuo
  6. 6
    أخرىThe residue was purified by column chromatography (silica gel, EtOAc/hexane)

الإجراء التجريبي

A mixture of 4-(benzyloxy)aniline (1010 mg), DIEA (1.771 mL) and methyl 2-fluoro-4-(trifluoromethyl)pyridine-3-carboxylate (1130 mg) in NMP (10 mL) was stirred at 150° C. for 2 h and at 200° C. for 1 h under microwave irradiation. The mixture was poured into water, and the mixture was extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (silica gel, EtOAc/hexane) to give the title compound (225 mg).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08846713B2uspto-grants-2014_09