Potassium Carbonate → 3-(4-Pyridinylthio)aniline

To a solution of 3-aminothiophenol (3.8 mL, 34 mmoles) in anh DMF (90 mL) was added 4-chloropyridine hydrochloride (5.4 g, 35.6 mmoles) followed by K2CO3 (16.7 g, 121 mmoles). The reaction mixture was stirred at room temp. for 1.5 h, then diluted with EtOAc (100 mL) and water (100 mL). The aqueous layer was back-extracted with EtOAc (2×100 mL). The combined organic layers were washed with a saturated NaCl solution (100 mL), dried (MgSO4), and concentrated under reduced pressure. The residue was filtered through a pad of silica (gradient from 50% EtOAc/50% hexane to 70% EtOAc/30% hexane) and the resulting material was triturated with a Et2O/hexane solution to afford the desired product (4.6 g, 66%): TLC (100% ethyl acetate) Rf 0.29; 1H-NMR (DMSO-d6) δ 5.41 (s, 2H), 6.64-6.74 (m, 3H), 7.01 (d, J=4.8, 2H), 7.14 (t, J=7.8 Hz, 1H), 8.32 (d, J=4.8, 2H).

1. extractionThe aqueous layer was back-extracted with EtOAc (2×100 mL)
2. washThe combined organic layers were washed with a saturated NaCl solution (100 mL)
3. dry with materialdried (MgSO4)
4. concentrationconcentrated under reduced pressure
5. filtrationThe residue was filtered through a pad of silica (gradient from 50% EtOAc/50% hexane to 70% EtOAc/30% hexane)
6. customthe resulting material was triturated with a Et2O/hexane solution

ORD record

ord-0df348cfa5d443e6b14515d0b27cc404

Source dataset

uspto-grants-2008_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07329670B1