Potassium Phosphate, Tribasic → 5-(3-(6-(1-pyrrolidinyl)-2-pyridinyl)-1H-indol-5-yl)-1,3,4-thiadiazol-2-amine

Participants

Reaction Conditions

Reaction Steps

A glass microwave reaction vessel was charged with 2-(pyrrolidin-1-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (46 mg, 0.17 mmol, CombiPhos Catalysts, Inc.) and 5-(3-iodo-1-tosyl-1H-indol-5-yl)-1,3,4-thiadiazol-2-amine (060 g, 0.12 mmol) in 66% IPA in H2O (1 mL) followed by Amphos (4 mg, 6 μmol), potassium phosphate (0.077 g, 0.36 mmol). The mixture was stirred and heated in a Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Uppsala, Sweden) at 100° C. for 10 min. The aqueous layer was removed and the resulting mixture was concentrated in vacuo and purified by preparative HPLC. The product was dissolved in p-dioxane (1 mL) and aq. NaOH (1 M, 0.1 mL) was added. The solution was heated in a microwave at 100° C. for 10 min, and purified by preparative HPLC to give 5-(3-(6-(1-pyrrolidinyl)-2-pyridinyl)-1H-indol-5-yl)-1,3,4-thiadiazol-2-amine (3 mg, 8%). MS (ESI, pos. ion) m/z: 364 (M+1). 1H NMR (400 MHz, CD3OD) δ ppm 8.23 (1H, s), 8.00 (1H, s), 7.91 (1H, dd, J=9.0, 7.6 Hz), 7.65 (1H, d, J=8.6 Hz), 7.58 (1H, d, J=8.6 Hz), 7.09 (1H, d, J=7.2 Hz), 6.85 (1H, d, J=9.0 Hz), 3.60-3.68 (4H, m), 2.06-2.14 (4H, m).

Provenance & Evidence