6-chloro-1H-indole-5-carbonitrile

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

Procedure: To a solution of 242 (43 mg, 0.24 mmol) in MeOH (10 mL) and 7M NH3 in MeOH (5 mL) was added Raney nickel and the reaction mixture was stirred vigorously under hydrogen (1 atm.) at RT for 3 h. The reaction mixture was filtered through a pad of Celite® and concentrated under reduced pressure to afford (6-chloro-1H-indol-5-yl)methanamine (244) as pale oil: MS (ESI)=164.1 [M−NH2]+. The reaction mixture was filtered through a pad of Celite® concentrated under reduced pressure

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

Procedure: To a solution of 242 (43 mg, 0.24 mmol) in MeOH (10 mL) and 7M NH3 in MeOH (5 mL) was added Raney nickel and the reaction mixture was stirred vigorously under hydrogen (1 atm.) at RT for 3 h. The reaction mixture was filtered through a pad of Celite® and concentrated under reduced pressure to afford (6-chloro-1H-indol-5-yl)methanamine (244) as pale oil: MS (ESI)=164.1 [M−NH2]+. The reaction mixture was filtered through a pad of Celite® concentrated under reduced pressure

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 240 (50 mg, 0.284 mmol) in THF (100 mL) was added t-BuOK (160 mg, 1.42 mmol). The mixture was heated at 75° C. for 3 h during which the color of the reaction mixture changed from yellow to brown. After the mixture was cooled, it was partitioned between EtOAc (200 mL) and H2O (50 mL). The organic layer was separated, washed with brine, dried and concentrated in vacuo to afford 43 mg (86%) of 6-chloro-1H-indole-5-carbonitrile (242) as white solid: 1H NMR (500 MHz, DMSO-d6) (511.80 (s, 1H), 8.21 (s, 1H), 7.70 (s, 1H), 7.60 (d, 1H), 6.61 (d, 1H); MS (ESI) m/z=177.0 [M+1]+. After the mixture was cooled it was partitioned between EtOAc (200 mL) and H2O (50 mL) The organic layer was separated washed with brine dried concentrated in vacuo

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

Procedure: To a solution of 242 (43 mg, 0.24 mmol) in MeOH (10 mL) and 7M NH3 in MeOH (5 mL) was added Raney nickel and the reaction mixture was stirred vigorously under hydrogen (1 atm.) at RT for 3 h. The reaction mixture was filtered through a pad of Celite® and concentrated under reduced pressure to afford (6-chloro-1H-indol-5-yl)methanamine (244) as pale oil: MS (ESI)=164.1 [M−NH2]+. The reaction mixture was filtered through a pad of Celite® concentrated under reduced pressure

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 240 (50 mg, 0.284 mmol) in THF (100 mL) was added t-BuOK (160 mg, 1.42 mmol). The mixture was heated at 75° C. for 3 h during which the color of the reaction mixture changed from yellow to brown. After the mixture was cooled, it was partitioned between EtOAc (200 mL) and H2O (50 mL). The organic layer was separated, washed with brine, dried and concentrated in vacuo to afford 43 mg (86%) of 6-chloro-1H-indole-5-carbonitrile (242) as white solid: 1H NMR (500 MHz, DMSO-d6) (511.80 (s, 1H), 8.21 (s, 1H), 7.70 (s, 1H), 7.60 (d, 1H), 6.61 (d, 1H); MS (ESI) m/z=177.0 [M+1]+. After the mixture was cooled it was partitioned between EtOAc (200 mL) and H2O (50 mL) The organic layer was separated washed with brine dried concentrated in vacuo