Tin tetrachloride → HCID 67995580, compound

To a solution of ethyl 6-bromo-1H-indole-2-carboxylate (4.40 g, 16.41 mmol) in dichloromethane (70 mL) at 0° C. was added tin (IV) chloride in dichloromethane (20.51 mL, 20.51 mmol) over 15 min. The resulting yellow heterogeneous mixture was stirred at room temperature for 30 min before a solution 2-methyl-3-nitrobenzoyl chloride (4.42 g, 22.16 mmol) in nitromethane (70 mL) was added over 20 min. The mixture was stirred at room temperature for 4 hr and then poured into ice-cold water (200 mL). The resulting mixture was stirred at room temperature for 20 min and diluted with ethyl acetate (800 ml). The mixture was washed with water (100 mL), saturated NaHCO3 solution (2×100 ml), water (100 mL), and brine (100 mL). The organic solution was dried over anhydrous MgSO4. Removal of solvent under vacuum gave the desired product (7.04 g, 16.33 mmol, 99% yield) as yellow solid.

1. additionwas added over 20 min
2. stirringThe resulting mixture was stirred at room temperature for 20 min
3. washThe mixture was washed with water (100 mL), saturated NaHCO3 solution (2×100 ml), water (100 mL), and brine (100 mL)
4. dry with materialThe organic solution was dried over anhydrous MgSO4
5. customRemoval of solvent under vacuum

ORD record

ord-5eaaa4dd82914f7ab1ffe14613a9686d

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08685969B2