8-BroMo-iMidazo[1,2-a]pyridine-6-carboxylic acid ethyl ester synthesis
- Product Name:8-BroMo-iMidazo[1,2-a]pyridine-6-carboxylic acid ethyl ester
- CAS Number:957103-97-8
- Molecular formula:C10H9BrN2O2
- Molecular Weight:269.09
107-20-0
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850429-51-5
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957103-97-8
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Yield: 63%
Reaction Conditions:
with sodium hydrogencarbonate in ethanol;water for 17 h;Reflux;
Steps:
16; 8.3; 9.3; 10.3; 11.3; 12; 15.3 [03631 Step 3: 8-Bromo-imidazo[1,2-alpyridine-6-carboxylic acid ethyl ester
[0364] To a stirred solution of compound III (80 g; 32.6 mmol; 1 eq) in ethanol (1 L) were added sodium bicarbonate (54.83 g; 65.2 mmol; 2 eq) and chloroacetaldehyde solution (-50% aqueous solution, 212 mL; 163.2 mmol; 5 eq) dropwise and the resulting mixture was heated at reflux for 17 h. The mixture was then evaporated to dryness and the pH was adjusted to 7 using ice-cold saturated aqueous NaHCO3 solution and solid NaHCO3. The organic components were extracted from the aqueous phase with ethyl acetate (3 x 500 mL) and the organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and the solvent was removed in vacuo to obtain a dry residue which was purified by silica gel (230-400 mesh) column chromatography using 10-50% ethyl acetate/hexanes as the eluent to afford the title compound (55 g, 63%) as a brown solid. 1H NMR (DMSO-d6) ö 9.33 (s, 1H), 8.24 (s, 1H), 7.84 (s, 1H), 7.73 (s, 1H), 4.34 (q, 2H, J= 8Hz), 1.34 (t, 3H, J= 8Hz). LCMS:mlz = 268.8 [M+j, 270.8 [M+21, RT = 2.90 minutes, (Program P1, Column W).
References:
ASANA BIOSCIENCES, LLC;THOMPSON, Scott;VENKATESAN, Aranapakam;PRIESTLEY, Tony;KUNDU, Mrinal;SAHA, Ashis WO2015/95128, 2015, A1 Location in patent:Paragraph 0234; 0358; 0363; 0364; 0375; 0380; 0381; 0427
7252-83-7
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80 suppliers
$29.00/500 mg
957103-97-8
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$170.00/0.5 G
3167-49-5
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957103-97-8
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39658-41-8
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957103-97-8
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