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To a solution of 4-tertiary-butyl-dimethyl-silanyloxy methyl- 2H- l,2,3-triazol (40 g, 187 mmol, prepared according to the procedure described in US20150266867) in dimethylformamide (200 ml) was added potassium carbonate (28.4 g, 205 mmol) under stirring. After completion of 15 minutes of stirring a solution of 2-(2-bromoethoxy)- lH-isoindole- l,3(2H)- dione (50.5 g, 187 mmol, prepared according to the procedure described in PCT Int. Appl. 2000018790) was added. Continued stirring with continuous monitoring of the reaction. The progress of reaction was monitored by TLC (hexane: ethyl acetate, 5:5). After complete consumption of starting material the reaction mixture was filtered through celite bed to remove insolubles and filtrate was concentrated. The concentrated mass was added to water (400 ml) and extracted with ethyl acetate (2x 400 ml). The organic extracts were combined and washed with brine (200 ml), dried over anhydrous sodium sulphate. The volatiles were removed under reduced pressure yielded 67 g crude compound. The isomers were separated by column chromatography (100-200 mesh size silica gel) using hexane: ethyl acetate, 8:2 as an eluent. The non-polar isomer 2-{2-[4-(tertiary-butyl-dimethyl-silanyloxy methyl)-2H- l,2,3-triazol-2-yl]ethoxy}- lH-isoindole- l,3(2H)-dione was eluted at 12% ethyl acetate in hexane and yielded 24 g of the product. The mixture of polar isomers 2-{2-[4-(tertiary-butyl-dimethyl-silanyloxymethyl)- lH- l,2,3-triazol- l- yl]ethoxy}- lH-isoindole- l,3(2H)-dione and 2- {2-[5-(tertiary-butyl-dimethyl-silanyloxymethyl)- lH- l,2,3-triazol- l-yl]ethoxy}- lH-isoindole- l,3(2H)-dione was eluted at 45% ethyl acetate in hexane to obtain 12 g of the product.
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Reference:
Patent; WOCKHARDT LIMITED; TADIPARTHI, Ravikumar; PATIL, Vijaykumar Jagdishwar; DEKHANE, Deepak; SHAIKH, Mohammad Usman; BIRAJDAR, Satish; DOND, Bharat; PATEL, Mahesh Vithalbhai; (100 pag.)WO2017/81615; (2017); A1;,
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