Potassium Carbonate → 3,5-Dichloro-4-[(5-methylsulfonyl-3-nitro-2-thienyl)sulfanyl]pyridine

Reaction equation

[Na].[Cl:2][C:3]1[CH:4]=[N:5][CH:6]=[C:7]([Cl:10])[C:8]=1[SH:9].Br[C:12]1[S:13][C:14]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18].C(=O)([O-])[O-].[K+].[K+]>>[Cl:2][C:3]1[CH:4]=[N:5][CH:6]=[C:7]([Cl:10])[C:8]=1[S:9][C:12]1[S:13][C:14]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18]

Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 602073102-Bromo-5-methanesulfonyl-3-nitrothiophene

HCID 178527724HCID 178527724, compound

Product 1

HCID 469321453,5-Dichloro-4-[(5-methylsulfonyl-3-nitro-2-thienyl)sulfanyl]pyridineYield 9%

Procedure

3,5-dichloropyridine-4-thiol sodium salt prepared as in example 17 (0.160 g, 0.39 mmol) and 2-bromo-5-methylsulfonyl-3-nitro-thiophene (0.1 g, 0.36 mmol) were dissolved in N,N-dimethylformide (3 mL). To the above mixture, potassium carbonate (0.192 g, 1.39 mmol) was added. The resulting reaction mixture was stirred at ambient temperature for 5 hours. After this time, the reaction mixture was quenched with ice water and stirred at ambient temperature for 20 minutes and the resulting precipitate was collected by filtration, washed with water (10 mL) and dried in vacuo at 40° C. overnight. The solid was triturated with dichloromethane and diethyl ether to afford the title product as an off-white solid (35 mg, 9% yield). 1H NMR (400 MHz, d6-DMSO) δ: 9.03 (1H, s), 8.66 (1H, s), 3.56 (3H, s). MS m/z: 383.09 [M+H]+.