Electric Literature of 14389-06-1,Some common heterocyclic compound, 14389-06-1, name is 5-Chloro-7-methylindoline-2,3-dione, molecular formula is C9H6ClNO2, 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.
To a suspension of 3-bromo-l-(3-chloro-2-pyridinyl)-lH-pyrazole-5-carboxylic acid (see PCT Patent Publication WO 03/015519 for preparation) (97.6% purity, 3.25 g, 10.5 mmol) and 5-chloro-7-methylindoline-2,3-dione (K. Tsuji et al., Bioorg. Med. Chem. Letters, 2002, 12(17), pp 2427-2430) (1.96 g, 10.0 mmol) in dry acetonitrile (12 mL) was added 3-picoline (2.60 g, 28 mmol). The mixture was cooled to 0 C, and then methanesulfonyl chloride (1.48 g, 12.9 mmol) was added dropwise at 0-10 C. After stirring 5 minutes at this temperature, the mixture was warmed to room temperature for 2 hours. Then additional quantities of 3-picoline (0.37 g, 4.0 mmol) and methanesulfonyl chloride (0.24 g, 2.1 mmol) were added, and stirring was continued at room temperature for 3 hours. The mixture was cooled to 0 C, water (6 mL) was added dropwise, and stirring at 0-5 0C was continued for 1 hour. Then the mixture was filtered, and the solids were washed with 2:1 acetonitrile-water (3 x 3 mL), and dried under nitrogen to afford the 3-picoline salt of the title compound as a light green solid, 1.23 g. EPO
The synthetic route of 14389-06-1 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; WO2007/24833; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem