Water → HCID 14270008, compound

HRID 2174212Notes

Reaction equation

HRID 2174212 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][CH3:9])=[O:7].[H-].[Na+].F[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1.O>CN(C=O)C>[N+:19]([C:16]1[CH:17]=[CH:18][C:13]([N:1]2[CH:5]=[CH:4][CH:3]=[C:2]2[C:6]([O:8][CH3:9])=[O:7])=[CH:14][CH:15]=1)([O-:21])=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 136930Methyl pyrrole-2-carboxylate

Product 1

HCID 14270008HCID 14270008, compoundYield 664.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 1H-pyrrole-2-carboxylate (1 g, 8.0 mmol) was dissolved in DMF (14 mL). The mixture was cooled down at 0° C. and sodium hydride (350 mg, 8.8 mmol) was added. After 5 min 1-fluoro-4-nitro-benzene (1.13 mmol, 7.99 mmol) was added and the mixture stirred at 80° C. for 3 hours. Water was added, the solid collected by filtration and washed with water to give (i) (1.85 g). 1H NMR (400 MHz, DMSO) δ 8.30 (d, J=9.0 Hz, 2H), 7.87-7.49 (m, 2H), 7.38 (dd, J=2.7, 1.8 Hz, 1H), 7.13 (dd, J=3.9, 1.7 Hz, 1H), 6.41 (dd, J=3.8, 2.8 Hz, 1H), 3.66 (s, 3H).

Workup

  1. filtrationthe solid collected by filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-6f97ee27f8674b5c876fbfe423152149
Source dataset
uspto-grants-2015_06
Patent number
US09060515B2

Reaction notes

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