4-(3-methylsulfonylpropoxy)-1H-indole

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-(3-Methanesulfonyl-propoxy)-1H-indole (188.1 g), 2,4-dichloropyrimidine (221.25 g), HOBT (20.08 g), K2CO3 (143.68 g) and DMA (1.6 L) were heated to 85° C. for 20 h. IPA (5 was then added and the mixture was stirred for 20 min, then cooled to 0° C. for 3 h and filtered. The collected solid was rinsed with IPA and water, and the solid was dried in vacuo at 55° C. for 4 days to yield 1-(2-chloro-pyrimidin-4-yl)-4-(3-methanesulfonyl-propoxy)-1H-indole (94%). filtered The collected solid was rinsed with IPA and water the solid was dried in vacuo at 55° C. for 4 days

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-Chloro-3-(methanesulfonyl)-propane (160 g) was added to 1H-indol-4-ol (108.77 g) in 1 L MeCN, and 338 g K2CO3 and 13.36 g KI were added. The reaction mixture was stirred overnight at 80° C., then cooled and filtered through celite. The filtrate was vacuum distilled and solvent replaced with DCM (700 mL). The mixture was filtered, and the solvent removed in vacuo and replaced with MeOH (600 mL). The solvent was partially removed in vacuo at 40° C. and crystallization occurred. After cooling, additional MeOH was added and the slurry was filtered. The collected solid was rinsed with cold MeOH and dried overnight at 35° C. in vacuo under N2 to provide 4-(3-methanesulfonyl-propoxy)-1H-indole (82%). were added cooled filtered through celite distilled The mixture was filtered the solvent removed in vacuo The solvent was partially removed in vacuo at 40° C. crystallization After cooling additional MeOH was added the slurry was filtered The collected solid was rinsed with cold MeOH dried overnight at 35° C. in vacuo under N2

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-(3-Methanesulfonyl-propoxy)-1H-indole (188.1 g), 2,4-dichloropyrimidine (221.25 g), HOBT (20.08 g), K2CO3 (143.68 g) and DMA (1.6 L) were heated to 85° C. for 20 h. IPA (5 was then added and the mixture was stirred for 20 min, then cooled to 0° C. for 3 h and filtered. The collected solid was rinsed with IPA and water, and the solid was dried in vacuo at 55° C. for 4 days to yield 1-(2-chloro-pyrimidin-4-yl)-4-(3-methanesulfonyl-propoxy)-1H-indole (94%). filtered The collected solid was rinsed with IPA and water the solid was dried in vacuo at 55° C. for 4 days

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-Chloro-3-(methanesulfonyl)-propane (160 g) was added to 1H-indol-4-ol (108.77 g) in 1 L MeCN, and 338 g K2CO3 and 13.36 g KI were added. The reaction mixture was stirred overnight at 80° C., then cooled and filtered through celite. The filtrate was vacuum distilled and solvent replaced with DCM (700 mL). The mixture was filtered, and the solvent removed in vacuo and replaced with MeOH (600 mL). The solvent was partially removed in vacuo at 40° C. and crystallization occurred. After cooling, additional MeOH was added and the slurry was filtered. The collected solid was rinsed with cold MeOH and dried overnight at 35° C. in vacuo under N2 to provide 4-(3-methanesulfonyl-propoxy)-1H-indole (82%). were added cooled filtered through celite distilled The mixture was filtered the solvent removed in vacuo The solvent was partially removed in vacuo at 40° C. crystallization After cooling additional MeOH was added the slurry was filtered The collected solid was rinsed with cold MeOH dried overnight at 35° C. in vacuo under N2

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-(3-Methanesulfonyl-propoxy)-1H-indole (188.1 g), 2,4-dichloropyrimidine (221.25 g), HOBT (20.08 g), K2CO3 (143.68 g) and DMA (1.6 L) were heated to 85° C. for 20 h. IPA (5 was then added and the mixture was stirred for 20 min, then cooled to 0° C. for 3 h and filtered. The collected solid was rinsed with IPA and water, and the solid was dried in vacuo at 55° C. for 4 days to yield 1-(2-chloro-pyrimidin-4-yl)-4-(3-methanesulfonyl-propoxy)-1H-indole (94%). filtered The collected solid was rinsed with IPA and water the solid was dried in vacuo at 55° C. for 4 days

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-Chloro-3-(methanesulfonyl)-propane (160 g) was added to 1H-indol-4-ol (108.77 g) in 1 L MeCN, and 338 g K2CO3 and 13.36 g KI were added. The reaction mixture was stirred overnight at 80° C., then cooled and filtered through celite. The filtrate was vacuum distilled and solvent replaced with DCM (700 mL). The mixture was filtered, and the solvent removed in vacuo and replaced with MeOH (600 mL). The solvent was partially removed in vacuo at 40° C. and crystallization occurred. After cooling, additional MeOH was added and the slurry was filtered. The collected solid was rinsed with cold MeOH and dried overnight at 35° C. in vacuo under N2 to provide 4-(3-methanesulfonyl-propoxy)-1H-indole (82%). were added cooled filtered through celite distilled The mixture was filtered the solvent removed in vacuo The solvent was partially removed in vacuo at 40° C. crystallization After cooling additional MeOH was added the slurry was filtered The collected solid was rinsed with cold MeOH dried overnight at 35° C. in vacuo under N2