Water → N-(2-benzoyl-6-chloro-1H-indol-3-yl)methanesulfonamide

Temperature

120 °C

To a solution of ethyl 3-amino-2-benzoyl-6-chloro-1H-indole-1-carboxylate (step 2 of Example 1, 200 mg, 0.58 mmol) in pyridine (5 ml) was added methanesufonyl chloride (0.07 ml, 0.87 mmol). After stirring for 72 h, the mixture was poured into water (100 ml) and extracted with diethyl ether (100 ml). The organic extract was washed consecutively with 10% aqueous citric acid (50 ml), water (50 ml), saturated aqueous sodium bicarbonate (50 ml), water (50 ml) and brine (50 ml), and dried (MgSO4). After removal of solvent the residue (287 mg) was dissolved in DMF (5 ml) and LiI (362 mg, 2.7 mmol) was added. The mixture was heated at 120° C. for 5 h, cooled and partitioned between water (100 ml) and diethyl ether (100 ml). The organic layer was separated and washed with water (100 ml), brine (100 ml) and dried (MgSO4). After removal of solvent the residue was purified by flash chromatography eluting with ethyl acetate/hexane (1:4) to afford the title compound (59 mg, 29%) as a yellow powder.

1. extractionextracted with diethyl ether (100 ml)
2. extractionThe organic extract
3. washwas washed consecutively with 10% aqueous citric acid (50 ml), water (50 ml), saturated aqueous sodium bicarbonate (50 ml), water (50 ml) and brine (50 ml)
4. dry with materialdried (MgSO4)
5. customAfter removal of solvent the residue (287 mg)
6. dissolutionwas dissolved in DMF (5 ml)
7. temperaturecooled
8. custompartitioned between water (100 ml) and diethyl ether (100 ml)
9. customThe organic layer was separated
10. washwashed with water (100 ml), brine (100 ml)
11. dry with materialdried (MgSO4)
12. customAfter removal of solvent the residue
13. customwas purified by flash chromatography
14. washeluting with ethyl acetate/hexane (1:4)

ORD record

ord-cf9a7e4fafb947188ece151cfb0e10e6

Source dataset

uspto-grants-2001_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06277878B1