HRMS (ESI?): Calcd. 30 min, the response mix was diluted with ethyl acetate (10 mL) and quenched with saturated Chromocarb aqueous sodium bicarbonate alternative (15 mL). The organic stage was separated, cleaned with brine, dried out over sodium sulfate, and focused in vacuo successively. The residue was crystallized in hexane/ethyl acetate to cover the required amine 7 being a yellowish solid (85 mg, produce: 80%). 1H NMR (400 MHz, DMSO) 7.73C7.69 (m, 1H), 7.42 (dd, = 8.5, 1.0 Hz, 1H), 6.95 (dd, = 7.9, 1.0 Hz, 1H), 6.65 (brs, 2H), 6.41 (d, = 2.1 Hz, 1H), 6.21 (d, Rabbit Polyclonal to FZD9 = 2.1 Hz, 1H), 1.35 (s, 9H), 1.33 (s, 9H). The overall synthetic method of substances 9aC9n. To a remedy of amine 7 (41 mg, 0.1 mmol) in dried out pyridine (2 mL), substituted benzenesulfonyl Chromocarb chloride (1.5C2 eq.) was added. The response mixture was held at r.t. right away and poured right into a combination of 1 hydrochloric acidity (10 mL) and ethyl acetate (10 mL) while getting vigorously stirred. The organic phase was concentrated and separated in vacuo. The residue was dissolved in an assortment of methanol (10 mL) and 5 sodium hydroxide alternative (5 mL) and held at r.t. for 1 h. The mix was focused in vacuo to eliminate the methanol and was diluted with drinking water (3 mL) and filtered. The pure water stage was cleaned with ethyl acetate (3 mL 2) and concentrated hydrochloric acidity was added dropwise until pH = 4. The mix was filtered to cover the required sulfonamide 9aC9n as yellow solids (produce: 30C80%). = 0.35 (Petroleum ether: Acetone = 4:1). 1H NMR (400 MHz, DMSO-= 8.4 Hz, 1H), 7.39C7.33 (m, 3H), 7.32C7.26 (m, 2H), 7.07 (d, = 8.4 Hz, 1H), 6.83 (d, = 8.3 Hz, 1H), 6.78 (s, 1H), 6.56 (s, 1H), 4.71 (s, 2H). Chromocarb MS (ESI?) 396.0 (M ? H)?. HRMS (ESI?): Calcd. for C20H14NO6S? [M ? H]? = 0.33 (Petroleum ether: Acetone = 4:1). 1H NMR (400 MHz, DMSO-= 7.9 Hz, 2H), 7.73C7.56 (m, 4H), 7.02 (d, = 8.6 Hz, 1H), 6.79 (d, = 8.3 Hz, 1H), 6.72 (s, 1H), 6.53 (s, 1H). 13C NMR (151 MHz, DMSO) 183.76, 161.25, 160.24, 156.69, 155.58, 146.64, 139.10, 137.64, 133.67, 129.74, 126.69, 110.81, 107.30, 107.26, 103.46, 99.41, 95.48. MS (ESI?) 382.0 (M ? H)?. HRMS (ESI?): Calcd. for C19H12NO6S? [M ? H]? = 0.30 (Petroleum ether: Acetone = 4:1). 1H NMR (400 MHz, DMSO-= 8.7, 5.0 Hz, 2H), 7.69 (t, = 8.3 Hz, 1H), 7.49 (t, = 8.6 Hz, Chromocarb 2H), 7.02 (d, = 8.4 Hz, 1H), 6.80 (d, = 8.2 Hz, 1H), 6.73 (s, 1H), 6.54 (s, 1H). 13C NMR (151 MHz, DMSO) 183.80, 164.71 (d, = 252.8 Hz), 161.28, 160.25, 156.71, 155.58, 146.35, 137.68, 135.40, 129.91 (d, = 9.6 Hz), 117.02 (d, = 22.9 Hz), 110.84, 107.32, 107.26, 103.61, 99.50, 95.59. MS (ESI?) 399.9 (M ? H)?. HRMS (ESI?): Calcd. for C19H11FSimply no6S? [M ? Chromocarb H]? = 0.30 (Petroleum ether: Acetone = 4:1). 1H NMR (400 MHz, DMSO-= 8.4 Hz, 1H), 6.80 (d, = 8.3 Hz, 1H), 6.75 (s, 1H), 6.55 (s, 1H). 13C NMR (151 MHz, DMSO) 183.80, 161.27, 160.23, 158.20 (d, = 255.2 Hz), 156.68, 155.59, 137.66, 136.79 (d, = 7.8 Hz), 130.51, 126.51 (d, = 13.2 Hz), 125.40, 117.68 (d, = 20.1 Hz), 110.83, 107.33, 107.27, 103.54, 99.15, 95.27, 90.84. MS (ESI?) 399.9 (M ? H)?. HRMS (ESI?): Calcd. for C19H11FSimply no6S? [M ? H]? = 0.37 (Petroleum ether: Acetone = 4:1). 1H NMR (400 MHz, DMSO-= 8.2 Hz, 2H), 7.76C7.60 (m, 3H), 7.01 (d, = 8.4 Hz, 1H), 6.79 (d, = 8.4 Hz, 1H), 6.72 (s, 1H), 6.53 (s, 1H). 13C NMR (151 MHz, DMSO) 183.81, 161.30, 160.25, 156.72, 155.58, 146.23,.