ethyl 5-methoxy-1H-pyrrolo[3,2-b]pyridine-2-carboxylate synthesis
- Product Name:ethyl 5-methoxy-1H-pyrrolo[3,2-b]pyridine-2-carboxylate
- CAS Number:17322-90-6
- Molecular formula:C11H12N2O3
- Molecular Weight:220.22
17288-28-7
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Yield:-
Reaction Conditions:
with iron;ammonium chloride in tetrahydrofuran;ethanol;water; for 1 h;Heating / reflux;
Steps:
35
To a suspension of 3- (6-methoxy-3-nitropyridin-2-yl)-2-oxopropionic acid ethyl ester (Preparation 34,276mg, 1. 03MMOL) in THF (12ML) and ethanol (5ML) was added saturated aqueous ammonium chloride solution (5ML) and iron powder (346mg, 6. 18MMOL) in one portion. The reaction mixture was heated under reflux for lh then filtered whilst still hot through a celite plug, washing with hot ethyl acetate. The filtrate was cooled and washed with brine (20mL), dried (MGS04), filtered and adsorbed onto silica gel IN VACUO. Purification via flash column chromatography (SI02, ethyl acetate/hexanes, 1: 9) gave the title compound as a beige solid. SN (CDCl3): 1.40 (3H, t), 3.99 (3H, s), 4.41 (2H, q), 6.74 (1H, d), 7.20 (1H, m), 7.62 (1H, d), 9.27 (1H, s).
References:
WO2004/104001,2004,A2 Location in patent:Page 44
5467-69-6
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13472-85-0
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