1-benzylsulfanyl-3-bromo-2-methylbenzene

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

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Intermediate 83 (7 g, 23.87 mmol), pyrrolidin-2-one (4.06 g, 47.74 mmol), CuI (909 mg, 4.77 mmol), N,N′-dimethylethylene diamine (10.28 ml, 95.49 mmol) and K2CO3 (7.25 g, 52.52 mmol) were suspended in toluene (10 ml) under N2 and heated to 110° C. for 16 h. After cooling to RT the reaction mixture was quenched by the addition of 100 ml water and extracted with ethyl acetate (three times). The organic layers were combined and washed with water and sat. aq NaCl-solution, dried with Na2SO4, filtered and evaporated to dryness, and purified by silica gel chromatography. After cooling to RT the reaction mixture was quenched by the addition of 100 ml water extracted with ethyl acetate (three times) washed with water and sat. aq NaCl-solution dried with Na2SO4 filtered evaporated to dryness purified by silica gel chromatography

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,6-dibromotoluene (20 g, 100 mmol) in dioxane (160 ml) was stirred under argon. Then, DIPEA (30.9 ml, 160 mmol), xantphos (2.77 g, 4.8 mmol) and Pd2(dba)3 (2.4 g, 2.4 mmol) were added and the reaction was heated to 100° C. Phenyl-methanethiol (9.4 ml, 80 mmol) was slowly added and the reaction stirred for 6 h. The reaction was quenched by the addition of 150 ml of H2O. After extraction (three times) with ethyl acetate, the combined organic layers were washed with water, dried with Na2SO4, evaporated to dryness and the product was purified by silica gel chromatography. The reaction was quenched by the addition of 150 ml of H2O After extraction (three times) with ethyl acetate the combined organic layers were washed with water dried with Na2SO4 evaporated to dryness the product was purified by silica gel chromatography

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Intermediate 83 (7 g, 23.87 mmol), pyrrolidin-2-one (4.06 g, 47.74 mmol), CuI (909 mg, 4.77 mmol), N,N′-dimethylethylene diamine (10.28 ml, 95.49 mmol) and K2CO3 (7.25 g, 52.52 mmol) were suspended in toluene (10 ml) under N2 and heated to 110° C. for 16 h. After cooling to RT the reaction mixture was quenched by the addition of 100 ml water and extracted with ethyl acetate (three times). The organic layers were combined and washed with water and sat. aq NaCl-solution, dried with Na2SO4, filtered and evaporated to dryness, and purified by silica gel chromatography. After cooling to RT the reaction mixture was quenched by the addition of 100 ml water extracted with ethyl acetate (three times) washed with water and sat. aq NaCl-solution dried with Na2SO4 filtered evaporated to dryness purified by silica gel chromatography

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Intermediate 83 (7 g, 23.87 mmol), pyrrolidin-2-one (4.06 g, 47.74 mmol), CuI (909 mg, 4.77 mmol), N,N′-dimethylethylene diamine (10.28 ml, 95.49 mmol) and K2CO3 (7.25 g, 52.52 mmol) were suspended in toluene (10 ml) under N2 and heated to 110° C. for 16 h. After cooling to RT the reaction mixture was quenched by the addition of 100 ml water and extracted with ethyl acetate (three times). The organic layers were combined and washed with water and sat. aq NaCl-solution, dried with Na2SO4, filtered and evaporated to dryness, and purified by silica gel chromatography. After cooling to RT the reaction mixture was quenched by the addition of 100 ml water extracted with ethyl acetate (three times) washed with water and sat. aq NaCl-solution dried with Na2SO4 filtered evaporated to dryness purified by silica gel chromatography

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,6-dibromotoluene (20 g, 100 mmol) in dioxane (160 ml) was stirred under argon. Then, DIPEA (30.9 ml, 160 mmol), xantphos (2.77 g, 4.8 mmol) and Pd2(dba)3 (2.4 g, 2.4 mmol) were added and the reaction was heated to 100° C. Phenyl-methanethiol (9.4 ml, 80 mmol) was slowly added and the reaction stirred for 6 h. The reaction was quenched by the addition of 150 ml of H2O. After extraction (three times) with ethyl acetate, the combined organic layers were washed with water, dried with Na2SO4, evaporated to dryness and the product was purified by silica gel chromatography. The reaction was quenched by the addition of 150 ml of H2O After extraction (three times) with ethyl acetate the combined organic layers were washed with water dried with Na2SO4 evaporated to dryness the product was purified by silica gel chromatography

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,6-dibromotoluene (20 g, 100 mmol) in dioxane (160 ml) was stirred under argon. Then, DIPEA (30.9 ml, 160 mmol), xantphos (2.77 g, 4.8 mmol) and Pd2(dba)3 (2.4 g, 2.4 mmol) were added and the reaction was heated to 100° C. Phenyl-methanethiol (9.4 ml, 80 mmol) was slowly added and the reaction stirred for 6 h. The reaction was quenched by the addition of 150 ml of H2O. After extraction (three times) with ethyl acetate, the combined organic layers were washed with water, dried with Na2SO4, evaporated to dryness and the product was purified by silica gel chromatography. The reaction was quenched by the addition of 150 ml of H2O After extraction (three times) with ethyl acetate the combined organic layers were washed with water dried with Na2SO4 evaporated to dryness the product was purified by silica gel chromatography

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

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

Procedure: Intermediate 24 (14.08 g, 48 mmol) and pyrrolidin-2-one (4.9 g, 57.6 mmol) were converted to intermediate 25 as described in example 1; 1.5). The crude product (14.6 g) was used without purification in the next step. The crude product (14.6 g) was used without purification in the next step

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Intermediate 83 (7 g, 23.87 mmol), pyrrolidin-2-one (4.06 g, 47.74 mmol), CuI (909 mg, 4.77 mmol), N,N′-dimethylethylene diamine (10.28 ml, 95.49 mmol) and K2CO3 (7.25 g, 52.52 mmol) were suspended in toluene (10 ml) under N2 and heated to 110° C. for 16 h. After cooling to RT the reaction mixture was quenched by the addition of 100 ml water and extracted with ethyl acetate (three times). The organic layers were combined and washed with water and sat. aq NaCl-solution, dried with Na2SO4, filtered and evaporated to dryness, and purified by silica gel chromatography. After cooling to RT the reaction mixture was quenched by the addition of 100 ml water extracted with ethyl acetate (three times) washed with water and sat. aq NaCl-solution dried with Na2SO4 filtered evaporated to dryness purified by silica gel chromatography

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,6-dibromotoluene (20 g, 100 mmol) in dioxane (160 ml) was stirred under argon. Then, DIPEA (30.9 ml, 160 mmol), xantphos (2.77 g, 4.8 mmol) and Pd2(dba)3 (2.4 g, 2.4 mmol) were added and the reaction was heated to 100° C. Phenyl-methanethiol (9.4 ml, 80 mmol) was slowly added and the reaction stirred for 6 h. The reaction was quenched by the addition of 150 ml of H2O. After extraction (three times) with ethyl acetate, the combined organic layers were washed with water, dried with Na2SO4, evaporated to dryness and the product was purified by silica gel chromatography. The reaction was quenched by the addition of 150 ml of H2O After extraction (three times) with ethyl acetate the combined organic layers were washed with water dried with Na2SO4 evaporated to dryness the product was purified by silica gel chromatography