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

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

5synthesis methods

Product Name:METHYL 4-BROMO-1-METHYL-1H-PYRROLE-2-CARBOXYLATE
CAS Number:1196-90-3
Molecular formula:C7H8BrNO2
Molecular Weight:218.05

934-05-4 Synthesis

934-05-4
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$8.00/1g

74-88-4
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$15.00/10g

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

1196-90-3
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$22.00/100mg

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

124-41-4 Synthesis