Application of 72093-04-0 , The common heterocyclic compound, 72093-04-0, name is 3-Chloro-4-methylpyridine, molecular formula is C6H6ClN, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
EXAMPLE 32 Compound CM A solution of diisopropylamine (1.23 mL)in dry tetrahydrofuran (15 mL) is stirred and cooled to -70 C. under a nitrogen atmosphere. To this is added a 2.5M solution of n-butyl lithium in hexanes (3.52 mL) at -70 C. The mixture is stirred for 30 minutes then a solution of 3-chloro-4-methylpyridine (1.02 g) in dry tetrahydrofuran (10 mL) is added. The mixture is stirred for a further 40 minutes. A solution of 3-cyclopentyloxy-4,N-dimethoxy-N-methylbenzamide (2.23 g) in dry tetrahydrofuran (10 mL) is added and the mixture stirred at -70 C. for 30 minutes, -40 C. for 30 minutes, 0 C. for 30 minutes, and room temperature for 1 hour. A mixture of ethanol and hydrochloric acid 19:1 (40 mL) is added and then the reaction mixture is partitioned between brine (40 mL) and diethyl ether (40 mL). The ethereal phase is dried over sodium sulfate and concentrated in vacuo to give a pale yellow solid (3.0 g). The solid is triturated with diethyl ether and then purified by flash chromatography (ethyl acetate eluent on a silica column) to give a solid (1.6 g). The solid is triturated with diethyl ether, collected and dried to afford 1-(3-cyclopentyloxy-4-methoxyphenyl)-2-(3-chloropyrid-4-yl)ethanone (1.35 g) as a cream solid m.p. 124-125 C. ?Elemental analysis: C,66.2; H,5.89; N,4.12%; calculated for C19 H20 ClNO3: C,65.99; H,5.83;[N,4.05%.]
The synthetic route of 72093-04-0 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Rhone-Poulenc Rorer Limited; US5679696; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem