Sodium hydride → methyl 3-(4-nitrophenyl)-1H-pyrrole-2-carboxylate

HRID 227667

Reaction equation

HRID 227667 reaction equation
[H-].[Na+].CC1C=CC(S(/[CH:13]=[CH:14]/[C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)(=O)=O)=CC=1.[N+:24]([CH2:26][C:27]([O:29][CH3:30])=[O:28])#[C-:25]>O1CCCC1.O.C(OCC)(=O)C>[N+:21]([C:18]1[CH:17]=[CH:16][C:15]([C:14]2[CH:13]=[CH:25][NH:24][C:26]=2[C:27]([O:29][CH3:30])=[O:28])=[CH:20][CH:19]=1)([O-:23])=[O:22]

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 547815Methyl isocyanoacetateHCID 138738071-methyl-4-[(1E)-2-(4-nitrophenyl)ethenesulfonyl]benzene

Product 1

HCID 18616331methyl 3-(4-nitrophenyl)-1H-pyrrole-2-carboxylateYield 111.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

To a suspension of 1.62 g (40.63 mmol) of 60% sodium hydride in mineral oil in 100 cm3 of tetrahydrofuran is added dropwise over 25 minutes, at a temperature in the region of 20° C. under an argon atmosphere, a mixture of 5.87 g (19.35 mmol) of 1-[(E)-2-(4-methylphenyl)sulfonylvinyl]-4-nitrobenzene and 3.7 cm3 (38.7 mmol) of methyl isocyanoacetate dissolved in 150 cm3 of tetrahydrofuran. After stirring for 5 hours at a temperature in the region of 20° C., the reaction mixture is taken up in a mixture of 100 cm3 of water and 200 cm3 of ethyl acetate. The organic phase is washed with twice 100 cm3 of water and 150 cm3 of saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) to give 5.3 g of a brown oil, which is purified by flash chromatography [eluent: dichloromethane]. After concentrating the fractions under reduced pressure, 2.12 g of methyl 3-(4-nitrophenyl)-1H-pyrrole-2-carboxylate are obtained in the form of a yellow solid; M.W.=246, IE: m/z=246 M+, m/z=214 [M-CH3OH]+.

Workup

  1. additionis added dropwise over 25 minutes, at a temperature in the region of 20° C. under an argon atmosphere
  2. washThe organic phase is washed with twice 100 cm3 of water and 150 cm3 of saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-3da4cccee92f4a889bcf7673128033c1
Source dataset
uspto-grants-2009_07
Patent number
US07560571B2

Linked notes

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