methyl 5-(4-(tert-butoxycarbonyl(3-nitrophenyl)amino)pyridine-2-yl)-1H-pyrrole-3-carboxylate → methyl 5-(4-((3-nitrophenyl)amino)pyridin-2-yl)-1H-pyrrole-3-carboxylate

HRID 521766ノート

反応式

HRID 521766 の反応式
C(OC([N:8]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-:32])=[O:31])[CH:25]=1)[C:9]1[CH:14]=[CH:13][N:12]=[C:11]([C:15]2[NH:19][CH:18]=[C:17]([C:20]([O:22][CH3:23])=[O:21])[CH:16]=2)[CH:10]=1)=O)(C)(C)C>C1(C)C=CC=CC=1>[N+:30]([C:26]1[CH:25]=[C:24]([NH:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]3[NH:19][CH:18]=[C:17]([C:20]([O:22][CH3:23])=[O:21])[CH:16]=3)[CH:10]=2)[CH:29]=[CH:28][CH:27]=1)([O-:32])=[O:31]

参加物

3

反応物 1

HCID 67042276methyl 5-(4-(tert-butoxycarbonyl(3-nitrophenyl)amino)pyridine-2-yl)-1H-pyrrole-3-carboxylate

生成物 1

HCID 67042295methyl 5-(4-((3-nitrophenyl)amino)pyridin-2-yl)-1H-pyrrole-3-carboxylate収率 49%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Methyl 5-(4-(tert-butoxycarbonyl(3-nitrophenyl)amino)pyridine-2-yl)-1H-pyrrole-3-carboxylate (0.40 g, 0.91 mmol) was taken up in toluene (38 mL) and SiO2 (9.0 g) was added. The mixture stirred at reflux for 20 h. The mixture was cooled to rt and filtered over celite, washing with EtOAc. The filtrate was concentrated to a bright orange color. The solid was taken up in hexanes and filtered. The solid was then washed with CH2Cl2/hexanes to afford methyl 5-(4-((3-nitrophenyl)amino)pyridin-2-yl)-1H-pyrrole-3-carboxylate (0.15 g, 49% yield) as a bright yellow solid.

後処理

  1. temperatureat reflux for 20 h
  2. filtrationfiltered over celite
  3. washwashing with EtOAc
  4. concentrationThe filtrate was concentrated to a bright orange color
  5. filtrationfiltered
  6. washThe solid was then washed with CH2Cl2/hexanes

出典と根拠

ORDレコード
ord-adeac8f50f4f46cfbc7d508fc70d2b46
出典データセット
uspto-grants-2016_05
特許番号
US09328103B2

反応ノート

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