Tetrahydrofuran → (6-Bromo-1H-indol-3-yl)acetic acid

Participants

Reaction Conditions

Reaction Steps

Step E (2): To a solution of 2-(6-bromo-1H-indol-3-yl)-2-oxoacetic acid (780 mg, 2.9 mmol) from Step E (1) in MeOH/EtOH (20.0 mL/5.0 mL) was added 4-methylbenzenesulfonohydrazide (1.1 g, 5.8 mmol). The mixture was heated at reflux for 5 h. The solvent was removed. 15 mL of THF and NaBH4 (658 mg, 17.4 mmol) were then added. The reaction mixture was stirred at 50° C. overnight and then at an additional 6 h at 80° C. The reaction mixture was diluted with H2O and 1.0 N HCl and washed with EtOAc. The aqueous layer was concentrated and the residue was purified using reverse phase Prep-HPLC to give 18 mg of the title compound. MS (ESI) (M−H)+=251.98/254.01. 1H-NMR (500 MHz, CD3OD) δ 7.52 (s, 1 H), 7.46 (d, J=8.55 Hz, 1 H), 7.19 (s, 1 H), 7.14 (dd, J=8.55, 1.53 Hz, 1 H), 3.73 (s, 2 H).

Provenance & Evidence