Triethylamine → N-[4-(5-Cyano-1-methyl-1H-pyrrol-2-yl)phenyl]furan-2-carboxamide

HRID 1993943Notes

Reaction equation

HRID 1993943 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[O:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[C:28](Cl)=[O:29]>ClCCl.CCOCC.C(OCC)(=O)C>[C:14]([C:11]1[N:12]([CH3:13])[C:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:28]([C:24]3[O:23][CH:27]=[CH:26][CH:25]=3)=[O:29])=[CH:3][CH:4]=2)=[CH:9][CH:10]=1)#[N:15]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 682422-Furancarbonyl chlorideHCID 160504305-(4-aminophenyl)-1-methyl-1H-pyrrole-2-carbonitrile

Product 1

HCID 16037459N-[4-(5-Cyano-1-methyl-1H-pyrrol-2-yl)phenyl]furan-2-carboxamideYield 28.1%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-(4-Aminophenyl)-1-methyl-1H-pyrrole-2-carbonitrile (98 mg, 0.5 mmol) was dissolved in dichloromethane (2 mL) and triethylamine (87 μL, 0.6 mmol) was added. Furan-2-carbonyl chloride (54 μL, 0.55 mmol) was added and the mixture was stirred 16 hours. The mixture was diluted with 50% ether in ethyl acetate and washed with water, saturated NaHCO3, 2N HCl, brine, dried over MgSO4, and passed through a plug of silica gel. The solution was concentrated to give N-[4-(5-cyano-1-methyl-1H-pyrrol-2-yl)phenyl]-2-furamide (0.041 g).

Workup

  1. washwashed with water, saturated NaHCO3, 2N HCl, brine
  2. dry with materialdried over MgSO4
  3. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-48725a26b820409a8bc66ac2c298c645
Source dataset
uspto-grants-2010_01
Patent number
US07652062B2

Reaction notes

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