55589-47-4, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 55589-47-4, name is 3-Methylpicolinaldehyde. This compound has unique chemical properties. The synthetic route is as follows.
To a microwave vial was added 4-[6-(2,4-dimethylpyrazol-3-yl)pyridazin-3-yl]oxy- l,2,3,3a,4,5,6,6a-octahydrocyclopenta[c]pyrrole hydrochloride (12 mg, 0.04 mmol) in DCM (0.5 mL) and THF (0.5 mL). Next, 3-methyl-2-pyridinecarboxaldehyde (20.5 mu^, 0.18 mmol) was added followed by sodium triacetoxyborohydride (39 mg, 0.18 mmol). The resulting suspension was stirred at ambient temperature for 18h then analyzed by LCMS. To the reaction was added saturated NaHCCb, and extracted with chloroform/IPA (4: 1). The organic solvents were concentrated, and the crude product was dissolved in DMSO (1 mL) and purified using the Gilson (Acidic, 30 x 50 mm column, 15 – 60percent ACN/ 0.1percent aqueous TFA, 4 min run). Fractions containing the product were basified with saturated NaHCC and extracted with chloroform/IPA (4: 1). The solvents were concentrated to give the title compound (8.1 mg, 0.020 mmol, 55percent yield, 5: 1 dr) as a clear oil. LCMS (90 sec method): RT = 0.598, m/z = 405.2 [M + H]+. Major Product NMR (400 MHz, chloroform-^: delta 8.33 – 8.34 (m, 1H), 7.45 (d, J = 9.10 Hz, 1H), 7.42 – 7.44 (m, 1H), 7.39 (s, 1H), 7.07 – 7.11 (m, 1H), 6.98 (d, J = 9.10, 1H), 5.55 – 5.61 (m, 1H), 4.02 (s, 3H), 3.71 (s, 2H), 3.09 – 3.15 (m, 1H), 2.76 – 2.86 (m, 1H), 2.64 – 2.71 (m, 2H), 2.48 – 2.52 (m, 1H), 2.44 (s, 3H), 2.30 – 2.35 (m, 1H), 2.13 (s, 3H), 1.97 – 2.10 (m, 2H), 1.71 – 1.80 (m, 1H), 1.53 – 1.57 (m, 1H).
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Reference:
Patent; VANDERBILT UNIVERSITY; LINDSLEY, Craig W.; CONN, P. Jeffrey; ENGERS, Darren W.; TEMPLE, Kayla J.; (87 pag.)WO2019/89676; (2019); A1;,
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