(4-methylsulfonylphenyl)methanol

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2,5-dibromopyridine (474 mg, 2.00 mmol) and 4-(methanesulfonyl)benzyl alcohol (372 mg, 2.00 mmol) in tetrahydrofuran (5 mL) was cooled to −15° C. under N2 and potassium tert-butoxide (1.0M in tetrahydrofuran, 2.2 mL, 2.20 mmol) was added dropwise over 10 minutes. The mixture was stirred at 0° C. for 5.5 hours, poured into saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to give the title compound (210 mg, yield 31%). extracted with ethyl acetate The organic layer was washed with brine dried over anhydrous sodium sulfate concentrated under reduced pressure The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)

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

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2,5-dibromopyridine (474 mg, 2.00 mmol) and 4-(methanesulfonyl)benzyl alcohol (372 mg, 2.00 mmol) in tetrahydrofuran (5 mL) was cooled to −15° C. under N2 and potassium tert-butoxide (1.0M in tetrahydrofuran, 2.2 mL, 2.20 mmol) was added dropwise over 10 minutes. The mixture was stirred at 0° C. for 5.5 hours, poured into saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to give the title compound (210 mg, yield 31%). extracted with ethyl acetate The organic layer was washed with brine dried over anhydrous sodium sulfate concentrated under reduced pressure The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)

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

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2,5-dibromopyridine (474 mg, 2.00 mmol) and 4-(methanesulfonyl)benzyl alcohol (372 mg, 2.00 mmol) in tetrahydrofuran (5 mL) was cooled to −15° C. under N2 and potassium tert-butoxide (1.0M in tetrahydrofuran, 2.2 mL, 2.20 mmol) was added dropwise over 10 minutes. The mixture was stirred at 0° C. for 5.5 hours, poured into saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to give the title compound (210 mg, yield 31%). extracted with ethyl acetate The organic layer was washed with brine dried over anhydrous sodium sulfate concentrated under reduced pressure The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-(Methylthio)benzyl alcohol (50 mmol, 7.71 g) was dissolved in methanol (150 ml) and cooled to 0° C. Oxone® (110 mmol, 67.6 g) in water (250 ml) was added. The stirred mixture was warmed to room temperature after 5 minutes. After 40 minutes, the mixture was diluted with water (250 ml), and extracted with methylene chloride (300 ml, then 2×100 ml). The combined organic layers were dried (MgSO4), filtered through silica, and concentrated to afford the title compound (5.48 g, 58%) as a waxy solid. The stirred mixture was warmed to room temperature after 5 minutes extracted with methylene chloride (300 ml The combined organic layers were dried (MgSO4) filtered through silica concentrated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-(Methylthio)benzyl alcohol (50 mmol, 7.71 g) was dissolved in methanol (150 ml) and cooled to 0° C. Oxone® (110 mmol, 67.6 g) in water (250 ml) was added. The stirred mixture was warmed to room temperature after 5 minutes. After 40 minutes, the mixture was diluted with water (250 ml), and extracted with methylene chloride (300 ml, then 2×100 ml). The combined organic layers were dried (MgSO4), filtered through silica, and concentrated to afford the title compound (5.48 g, 58%) as a waxy solid. The stirred mixture was warmed to room temperature after 5 minutes extracted with methylene chloride (300 ml The combined organic layers were dried (MgSO4) filtered through silica concentrated

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

Procedure: Using the procedure outlined in intermediate 8 (step B) the product from step C was reacted with 4-(methylsulfonyl)benzyl alcohol to yield the title compound. MS (ESI) m/z 444 [M+H]+. GPR119 Human EC50: 0.26 nM

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

Procedure: 4-(Methylsulfonyl)benzyl alcohol (1.0 g, 5.4 mmol) was dissolved in DMF (12 mL), and sodium hydride (60 wt % dispersion in oil, 320 mg, 8 mmol) was added. The iodide from step A (2.35 g, 6.4 mmol) in DMF (12 mL) was added and the resulting solution was stirred at RT for 15 h. The solution was quenched with sat. NH4Cl, and EtOAc. The organic layer was washed with water and brine. The organic layer was dried over Na2SO4, filtered, and concentrated. The residue was purified via silica gel column chromatography (2/1 hexanes/EtOAc) which provided the title compound. The solution was quenched with sat. NH4Cl, and EtOAc The organic layer was washed with water and brine The organic layer was dried over Na2SO4 filtered concentrated The residue was purified via silica gel column chromatography (2/1 hexanes/EtOAc) which