Pyrrole-2-carboxaldehyde → 1-[(4,5-Dimethoxy-2-nitrophenyl)methyl]-1H-pyrrole-2-carboxaldehyde

HRID 2215129Notes

Reaction equation

[H-].[Na+].[NH:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH:8]=[O:9].[CH3:10][O:11][C:12]1[C:19]([O:20][CH3:21])=[CH:18][C:15]([CH2:16]Br)=[C:14]([N+:22]([O-:24])=[O:23])[CH:13]=1>CN(C)C=O.C(OCC)(=O)C>[CH3:10][O:11][C:12]1[C:19]([O:20][CH3:21])=[CH:18][C:15]([CH2:16][N:3]2[CH:7]=[CH:6][CH:5]=[C:4]2[CH:8]=[O:9])=[C:14]([N+:22]([O-:24])=[O:23])[CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of sodium hydride (0.724 g, 60% suspension in oil) in N,N-dimethyl formamide (50 mL) was added pyrrole 2-carboxaldehyde (1.7 g, 18.1 mmol) and the reaction mixture was stirred for 30 minutes. It was then cooled to 0° C. and 4,5-dimethoxy-2-nitrobenzyl bromide (5.0 g, 1 equiv) was added dropwise over 20 minutes. After the addition, the reaction mixture was stirred at room temperature for 3 hours. It was then diluted with ethyl acetate (450 mL), washed with water, dried over anhydrous magnesium sulfate, filtered and evaporated to dryness. The crude product was triturated with water, filtered and washed with water. This material was dried over anhydrous potassium carbonate in vacuo to provide the title compound as a yellow crystalline solid (4.97 g), m.p. 109–112° C., which was used in the next step.

Workup

additionAfter the addition
stirringthe reaction mixture was stirred at room temperature for 3 hours
washwashed with water
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
customevaporated to dryness
customThe crude product was triturated with water
filtrationfiltered
washwashed with water
dry with materialThis material was dried over anhydrous potassium carbonate in vacuo

Sources & evidence

ORD record: ord-978ca54f673f4a4483a4375c351e2aac
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07109193B2

Reaction notes

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