Sodium Carbonate → Ethyl 3-(4-bromophenyl)-4-cyano-5-ethyl-1-methyl-1H-pyrrole-2-carboxylate

HRID 1865109Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:16])[C:8]([CH2:14][CH3:15])=[C:9]([C:12]#[N:13])[C:10]=1I)=[O:5])[CH3:2].[Br:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1>C(Cl)Cl.O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:16])[C:8]([CH2:14][CH3:15])=[C:9]([C:12]#[N:13])[C:10]=1[C:21]1[CH:22]=[CH:23][C:18]([Br:17])=[CH:19][CH:20]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 4-cyano-5-ethyl-3-iodo-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (2.0 g, 6.0 mmol, prepared in preparation 38), 4-bromophenyl boronic acid (1.32 g, 6.6 mmol), 10 mL of Na2CO3 (2M) and 20 mL of dioxane is degassed under reduced pressure (−29 inches) for 30 minutes till no bubbles. Recharge with nitrogen. Add PdCl2 (PPh)4 (0.24 mmol). Well seal the flask and heat the mixture at 80° C. overnight. After cooling, water and methylene chloride are added to the reaction mixture. It is then extracted with methylene chloride. The organic layers are combined, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue is purified by flash chromatography to provide the title compound (1.71 g, 78%). MS(ES, m/e) 361.1(M+1), 380.1(M+18). Rf=0.35 (50% ether in hexanes).

Workup

customis degassed under reduced pressure (−29 inches) for 30 minutes till no bubbles
customWell seal the flask
temperatureAfter cooling
extractionIt is then extracted with methylene chloride
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue is purified by flash chromatography

Sources & evidence

ORD record: ord-53b1d3f9659a4ab69526e05f2b302fa5
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625932B2

Reaction notes

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