Methyl iodide → 6-Chloro-2-(methylthio)-3H-imidazo[4,5-c]pyridine

To a stirring solution of 6-chloro-1H-imidazo[4,5-c]pyridine-2(3H)-thione (1.49 g, 8.03 mmol) and potassium hydroxide (540 mg, 9.63 mmol) in anhydrous EtOH (49.7 mL) was added iodomethane (0.50 mL, 8.03 mmol). The reaction solution was stirred at RT for 3.5 h, and then partitioned between EtOAc (64 mL) and 2N HCl (11.3 mL). The aqueous layer was separated, and the pH was adjusted to a slightly basic pH with the addition of saturated NaHCO3, followed by extraction with EtOAc (100 mL). The combined organic layers were concentrated, and dried under vacuum to afford the title compound as a solid. LC-MS: calculated for C7H6ClN3S 199.00 observed m/e: 200.04 (M+H)+ (Rt 1.12/2.0 min).

1. custompartitioned between EtOAc (64 mL) and 2N HCl (11.3 mL)
2. customThe aqueous layer was separated
3. additionthe pH was adjusted to a slightly basic pH with the addition of saturated NaHCO3
4. extractionfollowed by extraction with EtOAc (100 mL)
5. concentrationThe combined organic layers were concentrated
6. customdried under vacuum

ORD record

ord-4ac2d1b3f27d407988d93f89fb8a9da0

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09290517B2