3-(3-Bromophenyl)propionic acid

To a stirred solution of 3-(3-Bromophenyl) propanoic acid (3.0 g, 13.1 mmol) was added to a solution of SOC12 (10 ml) and was stirred for 2 hours at 70C. The mixture was concentrated under reduced pressure. The residue was dissolved in CH2C12 (20 ml), then was added dropwise into the mixture of cyclopropanamine (1.17g, 19.6 mmol) and triethylamine (4.0 g, 39.3 mmol) at 0 C, then the reaction mixture was stirred overnight at ambient temperature. The reaction mixture was quenched with IN HC1 and the organic layer was washed with brine, dried, concentrated to residue. The residue was purified by chromatography (PE/EA: 1/1 to 1/2) to give the title compound as white solid (2.8 g, 79 %). 1H NMR (400 MHz, CDC13) 57.36 (m, 2H), 7.15 (m, 2H), 5.53 (s, 1H), 2.94 (t, 2H), 2.68 (s, 1H), 2.41 (t, 2H), 0.77(m, 2H), 0.44 (m, 2H). m/e 268 (M+H)+.General procedure: To a solution of carboxylic acid (1 equiv.) and SOCl2 (5 equiv) inCH2Cl2 (0.5 M) was added 3 drops of DMF. The reaction was refluxed at 55 C for 5 h. ThenCH2Cl2 and the excess SOCl2 (5 equiv) were removed by vacuum. The acyl chloride obtainedwas dissolved in CH2Cl2 (1 M) for the next step. After that, to a 0 C solution of8-Aminoquinoline (10.4 mmol, 1 equiv.) and NEt3 (1.05 equiv.) in CH2Cl2 (0.5 M) was added theacyl chloride (1.05 equiv.) solution dropwise over 10 min. The solution was allowed to warm toambient temperature and was stirred for 6 h. After that, the solution was washed with water (15mL), sat. NaHCO3 (15 mL) and brine (15 mL). The organic phase was dried over Na2SO4, concentrated and purified by flash chromatography to provide the desired product.Step 1: To a stirred solution of General procedure: A solution of carboxylic acid (1.3 equiv) and CDI (1.2-1.8 equiv) indry CH2Cl2 (0.4-0.7 M) was stirred at room temperature for 1.5-4 h.Sulfonamide 16 (1 equiv) dissolved in dry CH2Cl2 (0.4-0.5 M) and15-50 vol% DMF was added and the solution was heated to reflux for21 h. The solvent was removed and the residue was dissolved in a largequantity of EtOAc and washed with 0.1 M HCl (aq), sat. Na2CO3 (aq)and brine, dried over MgSO4, filtered and concentrated under reducedpressure. The crude product was dissolved in EtOH, Cs2CO3 (2 equiv)was added and the mixture was heated in a microwave reactor at 120 Cfor 1.5 h The solvent was removed and 1 M HCl (aq) was added. Theformed precipitation was filtered off and washed with EtOAc.

Molecular Weight:229.07
XLogP3:2.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:227.97859
Monoisotopic Mass:227.97859
Topological Polar Surface Area:37.3
Heavy Atom Count:12
Complexity:159
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes