2-Mercaptoethanol → 2-(6-Aminopyridin-3-ylthio)ethanol

Participants

Reaction Conditions

Reaction Steps

In a 100 mL round-bottomed flask, 5-bromo-2-(2,2,5,5-tetramethyl-1,2,5-azadisilolidin-1-yl)pyridine (502 mg, 1.59 mmol), 2-mercaptoethanol (124 mg, 112 μl, 1.59 mmol), xantphos (46.1 mg, 79.6 μmol) and Hunig's base (411 mg, 556 μl, 3.18 mmol) were combined with dioxane (10.0 ml) to give a light yellow solution. Pd2(dba)3 (36.4 mg, 39.8 μmol) was added and the mixture was evacuated and filled with argon. The reaction mixture was heated to 110° C. and stirred for 17 h under argon. The reaction mixture was cooled to 25° C., concentrated in vacuo and partitioned between 1M HCl and EtOAc. Separated and basified aqueous with 3M NaOH. The aqueous layer was extracted with EtOAc (3×125 mL). The organic layers were combined, washed with sat NaCl (1×25 mL), dried over Na2SO4 and concentrated in vacuo to a light yellow solid. The solid was dried under vacuum at 25° C. for 21 hrs to afford 0.259 g (96%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ: 7.94 (d, J=2.3 Hz, 1H), 7.45 (dd, J=8.7, 2.3 Hz, 1H), 6.40 (d, J=8.7 Hz, 1H), 6.03-6.20 (m, 2H), 4.77 (t, J=5.7 Hz, 1H), 3.37-3.51 (m, 2H), 2.67-2.76 (m, 2H).

Provenance & Evidence