تفاعل #1009320

ord-14632bbb5b6540cfaa3a4c5eea818ebb

معادلة التفاعل

CCN(CC)CC
triethylamine
CC(=O)Cl
acetyl chloride
COc1cccc(NCC(O)Cn2c3ccc(Br)cc3c3cc(Br)ccc32)c1
1-(3,6-dibromo-9H-carbazol-9-yl)-3-(3-methoxyphenylamino)propan-2-ol
CCC[CH2][Sn](=[O])[CH2]CCC
dibutyltin oxide
COc1cccc(N(CC(O)Cn2c3ccc(Br)cc3c3cc(Br)ccc32)C(C)=O)c1
N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-hydroxypropyl)-N-(3-methoxyphenyl)acetamide

المذيبات

ظروف التفاعل

درجة الحرارة
150°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىThe reaction vessel was purged with nitrogen
  2. 2
    أخرىsealed
  3. 3
    أخرىhad been consumed
  4. 4
    ترشيحThe heterogeneous solution was filtered under vacuum
  5. 5
    أخرىto yield a white solid
  6. 6
    أخرىThe crude product was used without purification

الإجراء التجريبي

Following a literature procedure (Morcuende, A.; Ors, M.; Valverde, S.; Herradón, B. J. Org. Chem. 1996, 5264-5270) triethylamine (14 Tl, 0.10 mmol) and acetyl chloride (8 Tl, 0.11 mmol) were added to a heterogeneous mixture of 1-(3,6-dibromo-9H-carbazol-9-yl)-3-(3-methoxyphenylamino)propan-2-ol (53 mg, 0.11 mmol) and dibutyltin oxide (5.5 mg, 0.022 mmol) in anhydrous toluene (1.5 ml). The reaction vessel was purged with nitrogen, sealed and heated under microwave radiation to 150° C. for 9 minutes. The reaction was monitored by lc/ms and all SM had been consumed. The heterogeneous solution was filtered under vacuum to yield a white solid. The crude product was used without purification.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US09278923B2uspto-grants-2016_03