1-(chloromethyl)-4-methylsulfonylbenzene

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: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: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: Sodium hydride (0.014 g, 0.583 mmol) was added to a solution of methyl 2-(5-methyl-6H-thieno[2,3-b]pyrrol-4-yl)acetate (0.109 g, 0.52 mmol) in DMF (5 mL) at 0° C. The mixture was stirred 1 h at 0° C. before sequential addition of the 1-(chloromethyl)-4-(methylsulfonyl)benzene (0.156 g, 0.762 mmol) and sodium iodide (0.0935 g, 0.624 mmol). The reaction mixture was allowed to warm up to ambient temperature over 4 h. EtOAc was added and the resulting solution washed with water. The layers were separated and the organic solution was dried over MgSO4, filtered and concentrated under reduced pressure. The crude material was purified by chromatography on silica gel (heptane/EtOAc: 80/20 to 50/50) to give the title compound (0.117 g, 59.6%): LC/MS (Table 1, Method b) Rt=2.45 min; MS m/z 395 (M+NH4)+. the resulting solution washed with water The layers were separated the organic solution was dried over MgSO4 filtered concentrated under reduced pressure The crude material was purified by chromatography on silica gel (heptane/EtOAc: 80/20 to 50/50)

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of intermediate 1 (3.0 g), potassium carbonate (3.70 g), 1-(chloromethyl)-4-(methylsulfonyl)benzene (2.74 g) and DMF (20 mL) was heated at 50° C. for 24 hours. The mixture was allowed to cool then poured into water (50 mL) and extracted with dichloromethane (100 mL). The extracts were combined, evaporated under reduced pressure and the residue purified (SiO2 chromatography, eluting with 2% methanol in dichloromethane) to give the sub-titled compound (2.0 g). to cool extracted with dichloromethane (100 mL) evaporated under reduced pressure the residue purified (SiO2 chromatography, eluting with 2% methanol in dichloromethane)

反応条件: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of intermediate 1 (3.0 g), potassium carbonate (3.70 g), 1-(chloromethyl)-4-(methylsulfonyl)benzene (2.74 g) and DMF (20 mL) was heated at 50° C. for 24 hours. The mixture was allowed to cool then poured into water (50 mL) and extracted with dichloromethane (100 mL). The extracts were combined, evaporated under reduced pressure and the residue purified (SiO2 chromatography, eluting with 2% methanol in dichloromethane) to give the sub-titled compound (2.0 g). to cool extracted with dichloromethane (100 mL) evaporated under reduced pressure the residue purified (SiO2 chromatography, eluting with 2% methanol in dichloromethane)