1H-Pyrrole-2-carboxylicacid,4-formyl-,methylester(9CI) synthesis
- Product Name:1H-Pyrrole-2-carboxylicacid,4-formyl-,methylester(9CI)
- CAS Number:40611-79-8
- Molecular formula:C7H7NO3
- Molecular Weight:153.14
1193-62-0
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40611-79-8
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1197-13-3
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Yield:-
Reaction Conditions:
with N,N-dimethyl-formamide;trichlorophosphate in dichloromethane at 0 - 20; for 0.5 h;Heating / reflux;
Steps:
5.i 1-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-4-(perhydro-1,4-oxazepine-4-carbonyl)-1H-pyrrole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide
Example 5 1-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-4-(perhydro-1,4-oxazepine-4-carbonyl)-1H-pyrrole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide (i) 4-Formyl-1H-pyrrole-2-carboxylic acid methyl ester and 5-formyl-1H-pyrrole-2-carboxylic acid methyl ester: Both formyl-pyrrole derivatives were prepared adopting a procedure described by C. Schmuck,Tetrahedron2001, 57, 3063: To DMF (1.61 g) was added POCl3 (3.37 g) dropwise under Ar at 0°C. The mixture was allowed to warm to RT after which it was diluted with DCM (11 mL). A solution of 1H-pyrrole-2-carboxylic acid methyl ester (2.51 g) in DCM (11 mL) was added dropwise. The mixture was refluxed for 30 min whereupon it was cooled to 10 °C and quenched with a solution of potassium acetate (10.8 g) in water (28 mL). The phases were separated and the aqueous layer was extracted with MTBE. The combined organic phases were washed with saturated aqueous K2CO3 solution and concentrated in vacuo. The residue was purified by flash column chromatography on silica (ethyl acetate / heptane 1:5) to yield 4-formyl-1H-pyrrole-2-carboxylic acid methyl ester (589 mg) and 5-formyl-1H-pyrrole-2-carboxylic acid methyl ester (1.60 g) as solids.
References:
Aventis Pharma Deutschland GmbH EP1568698, 2005, A1 Location in patent:Page/Page column 45-46
1193-62-0
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4885-02-3
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40611-79-8
84 suppliers
$34.00/250mg
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40611-79-8
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$34.00/250mg
35302-72-8
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40611-79-8
84 suppliers
$34.00/250mg