Electric Literature of 67058-71-3, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 67058-71-3 as follows.
To a suspension of NaH (60 % in mineral oil, 90 mg, 2.25 mmol) in DMF (4.2 mL) cooled at 0C was added a solution of 1-(1 H-pyrrolo[2,3-c]pyridin-3-yl)-ethanone (prepared according to J. Org. Chem. 2002, 67, 6226) (300 mg, 1.87 mmol) in DMF (4.2 mL) and the resulting suspension was stirred at 0C under nitrogen atmosphere for 30 min before slow addition of tert-butyl bromoacetate (277 mu, 1.87 mmol). The reaction mixture was allowed to reach RT and further stirred at RT for 1.5 h. After completion of the reaction, the mixture was purified first by catch-release on SiliaPrep Tosic Acid-(2×10 g) (Varian) (eluent: MeOH (50 mL) by 2 M ammonia in MeOH (50 mL)) to give a mixture of regioisomers: (3-acetyl-pyrrolo[2,3-c]pyridin- 1-yl)-acetic acid tert-butyl ester and (3-acetyl-pyrrolo[2,3-c]pyridin-6-yl)-acetic acid tert-butyl ester followed by flash column chromatography on silica gel (CH2CI2 to CH2CI2/MeOH 85-15) to give (3-acetyl-pyrrolo[2,3-c]pyridin-1-yl)-acetic acid tert-butyl ester as a yellow powder. TLC, Rf (CH2CI2/ MeOH 9-1) = 0.50; MS (UPLC/MS): 275.3 [M+H]+, 319.2 [M+HCOO]-; tR (HPLC conditions f): 1.28 min; 1 H-NMR (400 MHz, DMSO-d6): delta (ppm): 8.88 (s, 1 H), 8.50 (s, 1 H), 8.33 (d, 1 H), 8.06 (d, 1 H), 5.27 (s, 2H), 2.48 (s,3H), 1.45 (s, 9H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,67058-71-3, its application will become more common.
Reference:
Patent; NOVARTIS AG; ALTMANN, Eva; HOMMEL, Ulrich; LORTHIOIS, Edwige Liliane Jeanne; MAIBAUM, Juergen Klaus; OSTERMANN, Nils; QUANCARD, Jean; RANDL, Stefan Andreas; SIMIC, Oliver; VULPETTI, Anna; ROGEL, Olivier; WO2012/93101; (2012); A1;,
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