7-iodo-3,4-dihydro-2H-isoquinolin-1-one

反応条件: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 7-Iodo-3,4-dihydro-2H-isoquinolin-1-one (I-32b: 200 mg, 0.7326 mmol) in DMA (1 mL) was added to a stirred solution of Pd(dba)3 (4.02 mg, 0.0043 mmol), Zn dust (1.9 mg, 0.0293 mmol), Dppf (7.77 mg, 0.0095 mmol) in DMA (1 mL) previously degassed with argon for 15 mins. The reaction mixture was stirred for 5 mins. This was followed by the addition of Zn(CN)2 (51.6 mg, 0.4395 mmol) and the resulting mixture was heated to 120° C. for 4 hrs. The reaction was monitored by TLC (80% ethylacetate). The reaction mixture was diluted with ethylacetate and washed with 2N NH4OH solution. The organic layer was dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (70% ethylacetate in hexane) afforded 80 mg of the product (63.48% yield). previously degassed with argon for 15 mins washed with 2N NH4OH solution The organic layer was dried over Na2SO4 concentrated Purification by column chromatography on silica gel (70% ethylacetate in hexane)

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: NaNO2 (340 mg, 4.9382 mmol) was added to a solution of 7-amino-3,4-dihydro-2H-isoquinolin-1-one (I-32a: 800 mg, 4.9382 mmol) in concentrated HCl (2 mL) and water (2 mL) at 0° C. The reaction mixture was stirred at 0° C. for 15 minutes. The resulting diazonium salt solution was added portion wise to a vigorously stirred biphasic mixture of DCM (25 mL), potassium iodide (4.9 g, 29.6242 mmol), copper iodide (47 mg, 0.25 mmol) and water (8 mL). The resulting mixture was stirred at room temperature overnight. The reaction was monitored by TLC (80% ethylacetate in hexane). The reaction mixture was diluted with DCM. The organic layer was washed with 10% Na2S2SO3 solution, dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (50% ethylacetate in hexane) afforded 640 mg of the product (44.50% yield). The resulting mixture was stirred at room temperature overnight The organic layer was washed with 10% Na2S2SO3 solution dried over Na2SO4 concentrated Purification by column chromatography on silica gel (50% ethylacetate in hexane)