BenzaMide, 2-aMino-3-broMo-

Step A: To 2-amino-3-bromobenzoic acid (0.5 g, 2.3 mmol) in DMF (5 mL) at rt were added hydroxybenzatriazole (0.46 g, 3.0 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (0.53 g, 2.8 mmol), ammonium chloride (0.5 g, 9.7 mmol), and diisopropylethylamine (1.7 ml, 9.7 mmol). The mixture was purged with NA 100 mL round bottom flask with stir bar was charged with 30 (Combi-Blocks, 0.500 g, 3.0 mmol, 1 eq) and NHGeneral procedure: A sealed tube was charged with isatin 1 (1a 147 mg, 1.0 mmol), ammonia hydrate 2 (25%, 421 mg, 3.0 mmol) and H2O2 (30%, 227 mg, 2.0 mmol) at room temperature, and then solvent DMSO (4 mL) was added. The resulting mixture was stirred at 30 C in a sealed vessel under air after 4 h, then added 50 mL water to the mixture, extracted with CH3COOC2H5 3 times (3 x 50 mL). The extract was washed with 30% NaCl solution (V/V), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Petroleum ether/Ethyl acetate = 3:1) to yield the desired product 3a as a yellow solid (89% yield).General procedure: Cyanuric chloride (0.15mmol) was added to a mixture of 3a-3x (1mmol) and 4a (206mg, 1.2mmol) in CH3CN, MeOH or DMSO (3mL). The mixture was stirred at room temperature for 0.5-2h. After completion, the mixture was extracted with EtOAc three times. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography eluting with CH2Cl2/MeOH (30/1) to afford H1, A1-A23.General procedure: 2-Aminobenzamides (1 mmol) and 1, 1-dichloro-2-nitroethene (1.2 mmol) were added to 5 mL of water in a 25 mL round-bottom flask. Then stirred at corresponding temperature and corresponding reaction time, after completion, the product precipitated from the reaction mixture and can be easily separated by filtration, then give the pure products.1001) A sealed-tube vessel with stir bar was charged with 31 (0.2733 g, 1.3 mmol, 1 eq), 2-naphthaldehyde (Aldrich, 0.208 g, 1.33 mmol, 1.05 eq), and FeCl3 (0.103 g, 0.64 mmol, 0.5 eq). CH3CN/water (1:1, 3 mL) was added. The vessel was closed, and the mixture was heated to 170 C. overnight. After cooling to room temperature the reaction was diluted with water. The solids were collected via vacuum filtration. The filter cake was triturated with 1:1 EtOAc/DCM and air dried yielding 0.429 g (1.2 mmol, 94% yield) of 32 as a tan solid. Mass spectrum (ESI+): m/z=351 [M+1].

Molecular Weight:215.05
XLogP3:1.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:213.97418
Monoisotopic Mass:213.97418
Topological Polar Surface Area:69.1
Heavy Atom Count:11
Complexity:163
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes