2-bromobenzenesulfonyl chloride

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 2.51 g (˜0.017 mole) of freshly distilled 4-chloro-N-methylaniline (b.p. 102-103° C.) is added 4.26 g (˜0.017 mole) of 2-bromo-benzenesulfonyl chloride (98 w/w %). The mixture is stirred until hot. Ten percent sodium hydroxide is added dropwise with stirring until the solution is slightly alkaline. The 2-bromo-4′-chloro-N-methylbenzene-sulfonanilide is formed as viscous liquid. It is washed with water several times until the wash water is neutral. The compound is dried overnight at room temperature. The yield is 4.2 g (69% yield). 1H NMR (deuterioacetone): δ 6.8-7.9 (m, 8 ArH), 3.2 (s, 3H, N—CH3). with stirring until the solution

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Freshly distilled N-methylaniline (b.p. 196° C.) is prepared. To 1.07 g (0.01 mole) of the N-methylaniline is added 2.56 g (0.01 mole) of 2-bromobenzenesulfonyl chloride (98 w/w %). The mixture is stirred until hot. Ten percent sodium hydroxide is then added dropwise with stirring until the solution is slightly alkaline, and 2-bromo-N-methylbenzenesulfonanilide is formed as a viscous red-brown liquid. It is washed with water several times until the wash water is neutral to litmus paper. A viscous red-brown liquid is extracted with ether, and the ether layer is dried over magnesium sulfate, filtered and the solvent removed by evaporation. The yield of red-brown oil is 2.30 g (70% yield). 1H NMR (deuterioacetone): δ 7.1-8 (m, 9 ArH), 3.3 (s, 3H, N—CH3). with stirring until the solution

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Bromo-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide was prepared from 5-amino-4-bromo-3-methylisoxazole and 2-bromobenzenesulfonyl chloride according to the procedures described in Example 30. The crude product was purified by recrystallization from ethyl acetate/hexanes to give a crystalline solid, m.p. 84-86° C., yield 31%. The crude product was purified by recrystallization from ethyl acetate/hexanes to give a crystalline solid, m.p. 84-86° C., yield 31%

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (32 mg, 53%), from 5-fluoro-3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole (Example 4b, 30.6 mg, 0.133 mmol) and 2-bromophenylsulfonyl chloride (67.9 mg, 0.27 mmol); HRMS-FAB+ for C20H19N2SO2BrF calculated MH+ : 449.03348; found: 449.03240.

Conditions: temp:10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 125 mL erlenmyer flask immersed in an ice/water bath at 5° C. was added 14.2 mL (0.18 Mol) of 2-methoxyethanol and 40 mL of anhydrous pyridine. To the stirred solution was added 51 grams (0.20 Mol) of bromobenzenesulfonyl chloride in portions while keeping the temperature of the reaction below 7° C. After total addition the sulfonyl chloride, the reaction was stirred for one hour and allowed to warm to 10° C. Then the product mixture was poured into 200 mL of ice water and stirred rapidly for 30 min. The mother liquors were decanted and the remaining oily product was treated again with 200 mL of water and rapidly stirred for 30 min. To this mixture was added 400 mL of diethyl ether, and after brief stirring the organic layer was separated from the aqueous layer. The aqueous layer was extracted with 200 mL of diethyl ether and the combined organic layers were dried over magnesium sulfate overnight in the refrigerator at 5° C. The magnesium sulfate was removed by gravity filtration and the ether was removed in vacuo to afford 48 grams (0.16 Mol, 88% yield) of the desired product as a thick oil. This material was noted to crystallize when stored in the refrigerator for extended periods of time. Into a 125 mL erlenmyer flask immersed in an ice/water bath at 5° C. the temperature of the reaction below 7° C stirred rapidly for 30 min The mother liquors were decanted the remaining oily product was treated again with 200 mL of water rapidly stirred for 30 min To this mixture was added 400 mL of diethyl ether after brief stirring the organic layer was separated from the aqueous layer The aqueous layer was extracted with 200 mL of diethyl ether the combined organic layers were dried over magnesium sulfate overnight in the refrigerator at 5° C The magnesium sulfate was removed by gravity filtration the ether was removed in vacuo

Conditions: temp:0.00; pressure:0.00; stir: