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
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]+.
Workup
- dissolutionwere dissolved in N,N-dimethylformide (3 mL)
- customThe resulting reaction mixture
- customAfter this time, the reaction mixture was quenched with ice water
- stirringstirred at ambient temperature for 20 minutes
- filtrationthe resulting precipitate was collected by filtration
- washwashed with water (10 mL)
- customdried in vacuo at 40° C. overnight
- customThe solid was triturated with dichloromethane and diethyl ether
Sources & evidence
- ORD record
- ord-a444a1aff37243c884558a7bdf568b4a
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08680139B2
Reaction notes
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