37441-50-2,Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials.37441-50-2,A new synthetic method of this compound is introduced below.
A stirred mixture of methyl 6-BROMO-3-HYDROXYPYRIDINE-2-CARBOXYLATE (6.15 g, 26.5 mmol), 8-sultam (described in WO 02/30931-A2, Merck & Co. , Inc. , 2002) (3. 98 g, 29.4 mmol) and copper (I) oxide (5.75 g, 40.2 mmol) in anhydrous pyridine (100 mL) was heated at 130 C, under argon, for 6 h. The mixture was cooled, and the pyridine removed under reduced pressure. The residue was treated with CH2C12 (400 mL) and EDTA (0.35 M in H20, 300 ML, 105 mmol) and air was bubbled into the mixture for 18 h. The mixture was filtered through a pad of celite and the aqueous layer was saturated with solid NACI and extracted with CH2CLZ (4 x 250 mL). The combined organic extracts were dried (NA2S04), filtered, and concentrated in vacuo to afford a crude oil. The oil was dissolved in MEOH (400 mL) and conc. H2S04 (2 ML) and heated to reflux for 18 h, then allowed to cool to ambient temperature. Most of the solvent was removed in vacuo and the residual mixture was partitioned between CHZCLX (400 mL) and saturated NAHCO3 (400 mL). The aqueous layer was extracted further with CH2Cl2 (2 x 250 mL) and the combined organic extracts were dried (NA2S04), filtered, and concentrated in vacuo to afford a crude sample of the product. This crude product was partially purified by silica gel chromatography, eluting with a gradient of CH2C12 : MEOH-100 : 0 to 95: 5 to give a yellow solid that was crystallized from MEOH to afford the title compound as a pale yellow solid of sufficient purity for use in the next step. MS: FALZ = 287 (M + 1).
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Reference£º
Patent; MERCK & CO., INC.; WO2005/9962; (2005); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem