7-chloro-8-fluoro-3,4-dihydro-2H-isoquinolin-1-one

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

Procedure: Using analogous reaction conditions as described in Example 1, 7-chloro-8-fluoro-3,4-dihydro-2H-isoquinolin-1-one (I-33d: 150 mg, 0.753 mmol) was reacted with 3-iodo-4-methyl-pyridine (165 mg, 0.73 mmol), 1,4-dioxane (10 mL), copper iodide (143 mg, 0.075 mmol), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (32 mg, 0.225 mmol) and potassium phosphate (399 mg, 1.88 mmol) to afford the crude product. Purification by column chromatography on silica gel (1% methanol in CHCl3) afforded 60 mg of the product (27.6% yield). reaction conditions to afford the crude product Purification by column chromatography on silica gel (1% methanol in CHCl3)

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

Procedure: Using the same reaction procedure and workup as described in example 1, [2-(4-chloro-3-fluoro-phenyl)-ethyl]-carbamic acid ethyl ester (I-33c: 1.3 g, 5.30 mmol) in POCl3 (10 mL) was reacted with P2O5 (1.5 g, 10.60 mmol) at 110° C. for 1 hour to afford the crude product. Purification by column chromatography on silica gel (30% ethylacetate in hexane) afforded 150 mg of the product (14% yield). the same reaction procedure to afford the crude product Purification by column chromatography on silica gel (30% ethylacetate in hexane)