1H-indol-2-ylmethanamine;hydrochloride

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

Procedure: To a solution of (1H-indol-2-yl)methanamine hydrochloride (50 mg, 0.27 mmol, CASRN 21109-25-1) and DCM (2.5 mL) at RT were added sequentially TEA (50 μL, 0.36 mmol) and CDI (44 mg, 0.27 mmol) and the reaction was stirred at RT for 30 min. This solution was added to a solution of 28 (55 mg, 0.229 mmol) and TEA (95.7 μL, 0.687 mmol) in DCM (5 mL) and the combined solution was stirred overnight. This solution was loaded directly a SiO2 chromatography column and eluted with a gradient hexane/EtOAc (0 to 10% EtOAc) to afford 57 mg (61.1%) of I-114: 1H NMR (400 MHz, CDCl3) δ 9.28 (s, 1H), 8.07 (s, 1H), 7.54 (d, 1H, J=7.8 Hz), 7.34 (d, 1H, J=7.1 Hz), 7.12-7.17 (m, 1H), 7.04-7.08 (m, 1H), 6.31-6.32 (m, 1H), 4.99-5.03 (m, 1H), 4.87 (d, 1H, J=7.7 Hz), 4.50 (d, 2H, J=5.9 Hz), 4.34 (s, 2H), 3.94-4.04 (m, 3H), 3.65-3.69 (m, 2H), 3.49-3.56 (m, 2H), 2.66-2.71 (m, 2H), 1.98-2.04 (m, 2H), 1.46-1.57 (m, 2H); MS (APCI-pos) M+1=407.4. the combined solution was stirred overnight eluted with a gradient hexane/EtOAc (0 to 10% EtOAc) to afford 57 mg (61.1%) of I-114

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

Procedure: To a solution of (1H-indol-2-yl)methanamine hydrochloride (50 mg, 0.27 mmol, CASRN 21109-25-1) and DCM (2.5 mL) at RT were added sequentially TEA (50 μL, 0.36 mmol) and CDI (44 mg, 0.27 mmol) and the reaction was stirred at RT for 30 min. This solution was added to a solution of 28 (55 mg, 0.229 mmol) and TEA (95.7 μL, 0.687 mmol) in DCM (5 mL) and the combined solution was stirred overnight. This solution was loaded directly a SiO2 chromatography column and eluted with a gradient hexane/EtOAc (0 to 10% EtOAc) to afford 57 mg (61.1%) of I-114: 1H NMR (400 MHz, CDCl3) δ 9.28 (s, 1H), 8.07 (s, 1H), 7.54 (d, 1H, J=7.8 Hz), 7.34 (d, 1H, J=7.1 Hz), 7.12-7.17 (m, 1H), 7.04-7.08 (m, 1H), 6.31-6.32 (m, 1H), 4.99-5.03 (m, 1H), 4.87 (d, 1H, J=7.7 Hz), 4.50 (d, 2H, J=5.9 Hz), 4.34 (s, 2H), 3.94-4.04 (m, 3H), 3.65-3.69 (m, 2H), 3.49-3.56 (m, 2H), 2.66-2.71 (m, 2H), 1.98-2.04 (m, 2H), 1.46-1.57 (m, 2H); MS (APCI-pos) M+1=407.4. the combined solution was stirred overnight eluted with a gradient hexane/EtOAc (0 to 10% EtOAc) to afford 57 mg (61.1%) of I-114

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

Procedure: To a solution of (1H-indol-2-yl)methanamine hydrochloride (50 mg, 0.27 mmol, CASRN 21109-25-1) and DCM (2.5 mL) at RT were added sequentially TEA (50 μL, 0.36 mmol) and CDI (44 mg, 0.27 mmol) and the reaction was stirred at RT for 30 min. This solution was added to a solution of 28 (55 mg, 0.229 mmol) and TEA (95.7 μL, 0.687 mmol) in DCM (5 mL) and the combined solution was stirred overnight. This solution was loaded directly a SiO2 chromatography column and eluted with a gradient hexane/EtOAc (0 to 10% EtOAc) to afford 57 mg (61.1%) of I-114: 1H NMR (400 MHz, CDCl3) δ 9.28 (s, 1H), 8.07 (s, 1H), 7.54 (d, 1H, J=7.8 Hz), 7.34 (d, 1H, J=7.1 Hz), 7.12-7.17 (m, 1H), 7.04-7.08 (m, 1H), 6.31-6.32 (m, 1H), 4.99-5.03 (m, 1H), 4.87 (d, 1H, J=7.7 Hz), 4.50 (d, 2H, J=5.9 Hz), 4.34 (s, 2H), 3.94-4.04 (m, 3H), 3.65-3.69 (m, 2H), 3.49-3.56 (m, 2H), 2.66-2.71 (m, 2H), 1.98-2.04 (m, 2H), 1.46-1.57 (m, 2H); MS (APCI-pos) M+1=407.4. the combined solution was stirred overnight eluted with a gradient hexane/EtOAc (0 to 10% EtOAc) to afford 57 mg (61.1%) of I-114