1-bromo-4-ethylsulfonylbenzene

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:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-Bromo-4-ethylsulfanyl-benzene (5.0 g) was dissolved in acetic acid and potassium permanganate as a 3% solution in water (8 mL) was added. The reaction mixture was heated to 90° C. for 3 hrs, after which time the reaction was cooled to room temperature and partitioned between ethyl acetate and 2N NaOH solution (500 m) each. The organics were separated and washed with water (100 mL), dried over sodium sulfate and purified on biotage eluting with 90:10 hexanes : ethyl acetate to afford the title compound as a clear oil (2.70 g). 1H NMR (300 MHz, CDCl3): δ 1.30 (t, J=7.85 Hz, 3 H) 3.02 (q, J=7.54 Hz, 2 H), 7.40 (m, 4 H). after which time the reaction was cooled to room temperature partitioned between ethyl acetate and 2N NaOH solution (500 m) each The organics were separated washed with water (100 mL) dried over sodium sulfate purified on biotage eluting with 90:10 hexanes

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

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

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-Bromo-4-ethylsulfanyl-benzene (5.0 g) was dissolved in acetic acid and potassium permanganate as a 3% solution in water (8 mL) was added. The reaction mixture was heated to 90° C. for 3 hrs, after which time the reaction was cooled to room temperature and partitioned between ethyl acetate and 2N NaOH solution (500 m) each. The organics were separated and washed with water (100 mL), dried over sodium sulfate and purified on biotage eluting with 90:10 hexanes:ethyl acetate to afford the title compound as a clear oil (2.70 g). 1H NMR (300 MHz, CDCl3): δ 1.30 (t, J=7.85 Hz, 3 H) 3.02 (q, J=7.54 Hz, 2 H), 7.40 (m, 4 H). after which time the reaction was cooled to room temperature partitioned between ethyl acetate and 2N NaOH solution (500 m) each The organics were separated washed with water (100 mL) dried over sodium sulfate purified on biotage eluting with 90:10 hexanes

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-Bromo-4-ethylsulfanyl-benzene (5.0 g) was dissolved in acetic acid and potassium permanganate as a 3% solution in water (8 mL) was added. The reaction mixture was heated to 90° C. for 3 hrs, after which time the reaction was cooled to room temperature and partitioned between ethyl acetate and 2N NaOH solution (500 m) each. The organics were separated and washed with water (100 mL), dried over sodium sulfate and purified on biotage eluting with 90:10 hexanes:ethyl acetate to afford the title compound as a clear oil (2.70 g). 1H NMR (300 MHz, CDCl3): δ 1.30 (t, J=7.85 Hz, 3 H) 3.02 (q, J=7.54 Hz, 2 H), 7.40 (m, 4 H). after which time the reaction was cooled to room temperature partitioned between ethyl acetate and 2N NaOH solution (500 m) each The organics were separated washed with water (100 mL) dried over sodium sulfate purified on biotage eluting with 90:10 hexanes

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

Procedure: This material was prepared in analogy to example 148 step F) from 8-(2-chloro-benzenesulfonyl)-2,8-diaza-spiro[4.5]decan-1-one and 1-bromo-4-ethanesulfonyl-benzene. White solid. MS (ESI): 497.0 MH+).

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

Procedure: The title compound was prepared in analogy to example 133, step 4 from 1,4-dioxa-10-aza-dispiro[4.2.4.2]tetradecan-9-one (described in example 133 step 3) and 1-bromo-4-ethylsulfonylbenzene as light yellow solid. MS (m/e): 380.153 [MH+].

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Potassium carbonate (0.315 g) was added to a stirred solution of the product from step (i) (0.4 g) and ethyl-(4-bromo-phenyl)-sulfone (0.285 g) in NMP (10 ml) and the mixture heated at 90° C. for 1 h. The mixture was partitioned between water/ethylacetate, the organics separated, dried, and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 25% ethylacetate/isohexane. Yield 0.4 g The mixture was partitioned between water/ethylacetate the organics separated, dried evaporated under reduced pressure The residue was purified by chromatography on silica eluting with 25% ethylacetate/isohexane