Potassium Carbonate → Methyl 6-((2,4-dichlorobenzyl)sulfanyl)-3-(2-ethoxy-2-oxoethoxy)thieno[2,3-b]pyridine-2-carboxylate

HRID 591554Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]2[S:8][C:9]([C:18]([O:20][CH3:21])=[O:19])=[C:10]([O:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5]2=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[Cl:28][C:29]1[CH:36]=[C:35]([Cl:37])[CH:34]=[CH:33][C:30]=1[CH2:31][SH:32]>CS(C)=O>[Cl:28][C:29]1[CH:36]=[C:35]([Cl:37])[CH:34]=[CH:33][C:30]=1[CH2:31][S:32][C:2]1[N:7]=[C:6]2[S:8][C:9]([C:18]([O:20][CH3:21])=[O:19])=[C:10]([O:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5]2=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of methyl 6-chloro-3-(2-ethoxy-2-oxoethoxy)thieno[2,3-b]pyridine-2-carboxylate (126.4 mg) and DMSO (3.8 mL) were added K2CO3 (63.6 mg) and 2,4-dichlorobenzyl mercaptan (0.065 mL). The mixture was stirred at 80° C. for 3 h. The mixture was quenched with saturated aqueous NaHCO3 and extracted with EtOAc. The combined organic layer was washed successively with water and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (73.9 mg).

Workup

customThe mixture was quenched with saturated aqueous NaHCO3
extractionextracted with EtOAc
washThe combined organic layer was washed successively with water and brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record: ord-c6e10ae52fea4543b2a463e095520ce1
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238639B2

Reaction notes

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