1,2-Dichloroethane → HCID 59577496, compound

Participants

Reaction Steps

To a solution of EDC (370 mg, 1.9 mmol), piperidine (0.24 mL, 0.21 g, 2.4 mmol), DIEA (0.33 mL, 0.25 g, 1.9 mmol) and hydroxybenzotriazole (257 mg, 1.9 mmol) in DCM (15 mL) was added 5-(benzothiazol-2-yloxy)-1H-indole-2-carboxylic acid (500 mg, 1.6 mmol) and the reaction mixture was stirred (rt, 48 h). The reaction mixture was partitioned between saturated NaHCO3 (10 mL) and DCM (20 mL). The organic layer was separated and the aqueous layer was extracted with DCM (2×25 mL). The organic layer was dried, filtered and concentrated in vacuo. The resulting residue was purified by silica gel flash chromatography using EtOAc:hexane (0-70%) to provide the title compound as a colorless solid (374 mg, 63%). MS (ESI): mass calcd. for C21H19N3O2S, 377.1; m/z found, 378.2 [M+H]+. 1H NMR (400 MHz, CDCl3): 9.77 (5, 1H), 7.74 (d, J=7.6, 1H), 7.67-7.59 (m, 2H), 7.48 (d, J=8.8, 1H), 7.37 (t, J=7.1, 1H), 7.27-7.20 (m, 2H), 6.78 (d, J=1.3, 1H), 3.99-3.74 (m, 4H), 1.90-1.64 (m, J=11.3, 5.8, 6H).

Provenance & Evidence