4-bromo-N-(2-methoxyethyl)benzenesulfonamide

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: n-Butyllithium (2.5M in hexanes, 8.36 mL, 20.89 mmol) was added dropwise to a solution of 4-bromo-N-[2-(methoxy)ethyl]benzenesulfonamide (0.5 g, 1.72 mmol) and triisopropylborate (4.8 mL, 20.89 mmol) in THF (15 mL) at −78° C. The mixture was stirred at −78° C. for 3 h and allowed to warm up to ambient temperature, stirred at ambient temperature overnight. The mixture was quenched with water (5 mL) and concentrated. The crude product was purified by chromatography on a silica gel column using 0 to 30% 2M NH3 in MeOH/CH2Cl2 to give 400 mg (89%) of [4-({[2-(methoxy)ethyl]amino}sulfonyl)phenyl]boronic acid as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.06-7.28 (m, 4H), 3.25-3.19 (m, 2H), 3.16-3.06 (m, 3H), 2.88-2.74 (m, 2H); LRMS (ESI), m/z 258 (M−H). to warm up to ambient temperature stirred at ambient temperature overnight The mixture was quenched with water (5 mL) concentrated The crude product was purified by chromatography on a silica gel column

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 4-Bromo-N-[2-(methoxy)ethyl]benzenesulfonamide (512 mg, 87%) was prepared as a white solid from 4-bromobenzenesulfonyl chloride (511 mg, 2 mmol), 2-(methoxy)ethylamine (0.174 mL, 2 mmol) and triethylamine (0.836 mL, 6 mmol) in CH2Cl2 (10 mL) in a manner similar to Example 108, Step 1. 1H NMR (400 MHz, CDCl3): δ 7.77-7.67 (m, 2H), 7.66-7.59 (m, 2H), 4.86 (t, 1H, J=5.7 Hz), 3.45-3.34 (m, 2H), 3.25 (s, 3H), 3.14-3.04 (m, 2H); LRMS (ESI), m/z 294/296 (M+H).

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound was prepared from 7-difluoromethyl-3-ethynyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine (example C.2) (340 mg, 1.0 mmol) and 4-bromo-N-(2-methoxy-ethyl)-benzenesulfonamide (example B.28) (276 mg, 1.0 mmol) according to general procedure II. Obtained as a yellow solid (400 mg, 72%). MS (ISP) 551.3 [(M+H)+]; mp 184-186° C.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound was prepared from 7-difluoromethyl-3-ethynyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine (example C.2) (340 mg, 1.0 mmol) and 4-bromo-N-(2-methoxy-ethyl)-benzenesulfonamide (example B.28) (276 mg, 1.0 mmol) according to general procedure II. Obtained as a yellow solid (400 mg, 72%). MS (ISP) 551.3 [(M+H)+]; mp 184-186° C.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound was prepared from 3-ethynyl-7-trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine (example C.1) (355 mg, 1.0 mmol) and 4-bromo-N-(2-methoxy-ethyl)-benzenesulfonamide (example B.28) (276 mg, 1.0 mmol) according to general procedure II. Obtained as a yellow solid (400 mg, 70%). MS (ISP) 569.1 [(M+H)+]; mp 185-187° C.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound was prepared from 3-ethynyl-7-trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine (example C.1) (355 mg, 1.0 mmol) and 4-bromo-N-(2-methoxy-ethyl)-benzenesulfonamide (example B.28) (276 mg, 1.0 mmol) according to general procedure II. Obtained as a yellow solid (400 mg, 70%). MS (ISP) 569.1 [(M+H)+]; mp 185-187° C.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Prepared by general procedure III from 4-bromobenzenesulfonyl chloride (5.0 g, 20 mmol) and 2-methoxyethyl amine (1.62 g, 22 mmol) to give the title compound (5.5 g, 95%) as an off-white crystalline solid. MS (ISP) 294.1[(M+H)+].