1,3,3,7-tetramethylindol-2-one

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under an argon atmosphere 5.71 mL of a 1 molar lithium aluminium hydride solution in THF were added dropwise to 600 mg (2.85 mmol) 1,3,3,7-tetramethyl-1,3-dihydro-indol-2-one in 20 mL THF. The reaction mixture was stirred for 2.5 h at 60° C. and then cooled to RT. While cooling with the ice bath, saturated, aqueous sodium sulphate solution was slowly added dropwise and the resulting suspension was filtered through Celite. The filtrate was combined with EtOAc and saturated sodium chloride solution. The organic phase was dried on sodium sulphate, filtered and the filtrate was evaporated down. cooled to RT the resulting suspension was filtered through Celite The organic phase was dried on sodium sulphate filtered the filtrate was evaporated down

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under an argon atmosphere 5.71 mL of a 1 molar lithium aluminium hydride solution in THF were added dropwise to 600 mg (2.85 mmol) 1,3,3,7-tetramethyl-1,3-dihydro-indol-2-one in 20 mL THF. The reaction mixture was stirred for 2.5 h at 60° C. and then cooled to RT. While cooling with the ice bath, saturated, aqueous sodium sulphate solution was slowly added dropwise and the resulting suspension was filtered through Celite. The filtrate was combined with EtOAc and saturated sodium chloride solution. The organic phase was dried on sodium sulphate, filtered and the filtrate was evaporated down. cooled to RT the resulting suspension was filtered through Celite The organic phase was dried on sodium sulphate filtered the filtrate was evaporated down

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

Procedure: 2.00 g (50.0 mmol) sodium hydride (55%, suspension in mineral oil) were added at 0° C. to 2.34 g (3.58 mmol) 7-methyl-1,3-dihydro-indol-2-one in 20 mL DMF and the mixture was stirred for 30 min. Then 3.00 mL (48.2 mmol) iodomethane were added and the mixture was stirred for 2 h at RT. Ice water was added to the reaction mixture, then it was extracted with DCM and aqueous sodium hydrogen carbonate solution. The organic phase was dried on sodium sulphate, filtered and evaporated down i. vac. The residue was purified by preparative HPLC-MS. The fractions containing the product were combined and freeze-dried. the mixture was stirred for 2 h at RT it was extracted with DCM and aqueous sodium hydrogen carbonate solution The organic phase was dried on sodium sulphate filtered evaporated down i The residue was purified by preparative HPLC-MS The fractions containing the product freeze-dried

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under an argon atmosphere 5.71 mL of a 1 molar lithium aluminium hydride solution in THF were added dropwise to 600 mg (2.85 mmol) 1,3,3,7-tetramethyl-1,3-dihydro-indol-2-one in 20 mL THF. The reaction mixture was stirred for 2.5 h at 60° C. and then cooled to RT. While cooling with the ice bath, saturated, aqueous sodium sulphate solution was slowly added dropwise and the resulting suspension was filtered through Celite. The filtrate was combined with EtOAc and saturated sodium chloride solution. The organic phase was dried on sodium sulphate, filtered and the filtrate was evaporated down. cooled to RT the resulting suspension was filtered through Celite The organic phase was dried on sodium sulphate filtered the filtrate was evaporated down

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

Procedure: 2.00 g (50.0 mmol) sodium hydride (55%, suspension in mineral oil) were added at 0° C. to 2.34 g (3.58 mmol) 7-methyl-1,3-dihydro-indol-2-one in 20 mL DMF and the mixture was stirred for 30 min. Then 3.00 mL (48.2 mmol) iodomethane were added and the mixture was stirred for 2 h at RT. Ice water was added to the reaction mixture, then it was extracted with DCM and aqueous sodium hydrogen carbonate solution. The organic phase was dried on sodium sulphate, filtered and evaporated down i. vac. The residue was purified by preparative HPLC-MS. The fractions containing the product were combined and freeze-dried. the mixture was stirred for 2 h at RT it was extracted with DCM and aqueous sodium hydrogen carbonate solution The organic phase was dried on sodium sulphate filtered evaporated down i The residue was purified by preparative HPLC-MS The fractions containing the product freeze-dried