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 521766Notes

Reaction equation

HRID 521766 reaction equation
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]

Participants

3

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-adeac8f50f4f46cfbc7d508fc70d2b46
Source dataset
uspto-grants-2016_05
Patent number
US09328103B2

Reaction notes

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