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ChemicalBook CAS DataBase List METHYL 4-BROMO-1-METHYL-1H-PYRROLE-2-CARBOXYLATE
1196-90-3

METHYL 4-BROMO-1-METHYL-1H-PYRROLE-2-CARBOXYLATE synthesis

5synthesis methods
-

Yield: 986 mg

Reaction Conditions:

Stage #1:methyl 4-bromo-1H-pyrrole-2-carboxylate with sodium hydride in N,N-dimethyl-formamide at 0; for 0.5 h;Inert atmosphere;
Stage #2:methyl iodide in N,N-dimethyl-formamide at 20; for 18 h;

Steps:

2.1 Example 2: Preparation of l-methyl-4-pyridin-4-yl-lH-pyrrole-2-carboxylic acid amide Step 1: Preparation of 4-bromo-l-methyl-lH-pyrrole-2-carboxylic acid methyl ester
NaH (256 mg, 6.40 mmol) was added into DMF (5 mL) and stirred at 0 °C under nitrogen for 10 min. A solution of 4-bromo-lH-pyrrole-2-carboxylic acid methyl ester (1 g, 4.93 mmol) in DMF (5 mL) was added in 15 min at 0 °C. The resulting mixture was stirred at 0°C for 30 min. Mel (909 mg, 6.40 mmol) was added to the reaction mixture. After being stirred for another 18 h at room temperature, the mixture was poured into water, and then extracted with MTBE twice. The combined organic layers were washed with brine, and then dried over anhydrous Na2S04, then filtered and concentrated in vacuo. The residue was purified by column chromatography to afford 4-bromo-l -methyl- lH-pyrrole-2-carboxylic acid methyl ester (986 mg) as a solid.

References:

F. HOFFMANN-LA ROCHE AG;HOFFMANN-LA ROCHE INC.;HAN, Xingchun;JIANG, Min;MAYWEG, Alexander V.;WANG, Lisha;YANG, Song WO2014/154723, 2014, A1 Location in patent:Page/Page column 31-32

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