6-amino-7-bromo-2,3-dihydro-1H-inden-1-one

A solution of Example 129B (2.0516 g, 13.94 mmol) in 9:1 CHCl3.DMF (52 mL) was slowly treated with Br2 (0.71 mL, 13.94 mmol), stirred for 1 hour, and filtered. The filter cake was dried under vacuum to provide the desired product (2.7127 g, 63percent). MS (ESI(+)) m/e 226, 228 (M+H)+; MS (ESI(-)) m/e 225, 227 (M-H)-; 1H NMR (300 MHz, DMSO-d6) δ 7.28 (dt, 1H), 7.17 (d, 1H), 5.87 (br s, 3H), 2.89 (m, 2H), 2.62 (m, 2H).EXAMPLE 129C 6-amino-7-bromo-1-indanone [0368] A solution of Example 129B (2.0516 g, 13.94 mmol) in 9:1 CHCl3.DMF (52 mL) was slowly treated with Br2 (0.71 mL, 13.94 mmol), stirred for 1 hour, and filtered. The filter cake was dried under vacuum to provide the desired product (2.7127 g, 63percent). MS (ESI(+)) m/e 226, 228 (M+H)+; MS (ESI(-)) m/e 225, 227 (M-H)-; 1H NMR (300 MHz, DMSO-d6) δ 7.28 (dt, 1H), 7.17 (d, 1H), 5.87 (br s, 3H), 2.89 (m, 2H), 2.62 (m, 2H).c) Preparation of; A solution of c) Preparation of A solution of EXAMPLE 129C EXAMPLE 129D N-(4-bromo-3-oxo-2, 3-dihydro-1H-inden-5-yl)benzenesulfonamide [0369] A solution of Example 129C (1.0808 g, 3.52 mmol) in pyridine (17.5 mL) was treated with phenylsulfonyl chloride (0.58 mL, 4.58 mmol), stirred for 2 hours, diluted with CH2Cl2, washed with 1N HCl (3×50 mL) and brine (50 mL), dried (MgSO4), filtered, and concentrated. The residue was purified by flash column chromatography on silica gel with 9:1 hexanes/ethyl acetate to provide the desired product (450 mg, 35%); MS (ESI(+)) m/e 368 (M+H)+; MS (ESI(-)) m/e 364, 366 (M-H)-; 1H NMR (300 MHz, DMSO-d6) delta 7.70 (m, 2H), 7.63 (m, 1H), 7.56 (m, 2H), 7.51 (m, 1H), 7.42 (m, 1H), 3.00 (m, 2H), 2.66 (m, 2H).EXAMPLE 129C b) Preparation of; A solution of 6-aminoindanone (12 g, 81.6 mmol) in N, N-dimethylformamide (220 ml) is treated with N-bromosuccinimide (14.5 g, 81.6 mmol) in portions over a period of one hour and stirred for one hour. Evaporation of the solvent and water/dichloromethane workup followed by purification by chromatography with EtOAc/hexane (1 :3) as eluent gives the product b) Preparation of A solution of 6-aminoindanone (12 g, 81.6 mmol) in N, N-dimethylformamide (220 ml) is treated with N-bromosuccinimide (14.5 g, 81.6 mmol) in portions over a period of one hour and stirred for one hour. Evaporation of the solvent and water/dichloromethane workup followed by purification by chromatography with EtOAc/hexane (1:3) as eluent gives the product EXAMPLE 129C b) Preparation of; A solution of 6-aminoindanone (12 g, 81.6 mmol) in N, N-dimethylformamide (220 ml) is treated with N-bromosuccinimide (14.5 g, 81.6 mmol) in portions over a period of one hour and stirred for one hour. Evaporation of the solvent and water/dichloromethane workup followed by purification by chromatography with EtOAc/hexane (1 :3) as eluent gives the product b) Preparation of A solution of 6-aminoindanone (12 g, 81.6 mmol) in N, N-dimethylformamide (220 ml) is treated with N-bromosuccinimide (14.5 g, 81.6 mmol) in portions over a period of one hour and stirred for one hour. Evaporation of the solvent and water/dichloromethane workup followed by purification by chromatography with EtOAc/hexane (1:3) as eluent gives the product

Molecular Weight:226.07
XLogP3:1.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:224.97893
Monoisotopic Mass:224.97893
Topological Polar Surface Area:43.1
Heavy Atom Count:12
Complexity:207
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes