tert-Butyl [3-hydroxypropyl][2-(3,4-dimethoxyphenyl)ethyl]carbamate

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

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

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: DIAD (1.15 mL, 5.87 mmol) was added dropwise to a solution of 4-bromo-6,6-dimethyl-2-(4-methyl-3-nitrophenyl)-1H-imidazo[4,5-h]isoquinoline-7,9(6H,8H)-dione (1.3 g, 2.93 mmol), tert-butyl [2-(3,4-dimethoxyphenyl)ethyl](3-hydroxypropyl)carbamate (from Example 1) (1.99 g, 5.87 mmol), and PPh3 (1.54 g, 5.87 mmol) in THF (14.7 mL). The reaction mixture was stirred at 25° C. for 30 min, then was concentrated under reduced pressure. The residue was purified twice by flash chromatography (40-63μ silica gel) first with hexane:EtOAc 1:1 and then with CH2Cl2:acetone 95:5 to give the title compound (789.6 mg, 35% yield). was concentrated under reduced pressure The residue was purified twice by flash chromatography (40-63μ silica gel) first with hexane:EtOAc 1:1

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

Procedure: DIAD (1.92 mL, 9.75 mmol) was slowly added to an ice-cold solution of 7-amino-4,4-dimethyl-8-nitroisoquinoline-1,3(2H,4H)-dione (2.03 g, 8.14 mmol; prepared according to the method described in DE 3410168), tert-butyl [3-hydroxypropyl][2-(3,4-dimethoxyphenyl)ethyl]carbamate (3.31 g, 9.78 mmol), and PPh3 (2.56 g, 9.76 mmol) in THF (40 mL). The reaction mixture was allowed to warm to room temperature and was stirred at this temperature for 16 h. The mixture was concentrated under reduced pressure and the residue was purified by flash chromatography (40-63μ silica gel, hexane:EtOAc 1:1) to give the title compound (4.29 g, 92% yield). prepared The mixture was concentrated under reduced pressure the residue was purified by flash chromatography (40-63μ silica gel, hexane:EtOAc 1:1)

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

Procedure: DIAD (1.92 mL, 9.75 mmol) was slowly added to an ice-cold solution of 7-amino-4,4-dimethyl-8-nitroisoquinoline-1,3(2H,4H)-dione (2.03 g, 8.14 mmol; prepared according to the method described in DE 3410168), tert-butyl [3-hydroxypropyl][2-(3,4-dimethoxyphenyl)ethyl]carbamate (3.31 g, 9.78 mmol), and PPh3 (2.56 g, 9.76 mmol) in THF (40 mL). The reaction mixture was allowed to warm to room temperature and was stirred at this temperature for 16 h. The mixture was concentrated under reduced pressure and the residue was purified by flash chromatography (40-63μ silica gel, hexane:EtOAc 1:1) to give the title compound (4.29 g, 92% yield). prepared The mixture was concentrated under reduced pressure the residue was purified by flash chromatography (40-63μ silica gel, hexane:EtOAc 1:1)

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

Procedure: DIAD (1.92 mL, 9.75 mmol) was slowly added to an ice-cold solution of 7-amino-4,4-dimethyl-8-nitroisoquinoline-1,3(2H,4H)-dione (2.03 g, 8.14 mmol; prepared according to the method described in DE 3410168), tert-butyl [3-hydroxypropyl][2-(3,4-dimethoxyphenyl)ethyl]carbamate (3.31 g, 9.78 mmol), and PPh3 (2.56 g, 9.76 mmol) in THF (40 mL). The reaction mixture was allowed to warm to room temperature and was stirred at this temperature for 16 h. The mixture was concentrated under reduced pressure and the residue was purified by flash chromatography (40-63μ silica gel, hexane:EtOAc 1:1) to give the title compound (4.29 g, 92% yield). prepared The mixture was concentrated under reduced pressure the residue was purified by flash chromatography (40-63μ silica gel, hexane:EtOAc 1:1)