Phosphorus oxychloride → Methyl 6-chloro-3-(2-ethoxy-2-oxoethoxy)thieno[2,3-b]pyridine-2-carboxylate

HRID 591553Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:21])[CH2:5][O:6][C:7]1[C:15]2[C:10](=[N+:11]([O-])[CH:12]=[CH:13][CH:14]=2)[S:9][C:8]=1[C:17]([O:19][CH3:20])=[O:18])[CH3:2].P(Cl)(Cl)([Cl:24])=O>C1(C)C=CC=CC=1>[Cl:24][C:12]1[N:11]=[C:10]2[S:9][C:8]([C:17]([O:19][CH3:20])=[O:18])=[C:7]([O:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:21])[C:15]2=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of methyl 3-(2-ethoxy-2-oxoethoxy)thieno[2,3-b]pyridine-2-carboxylate 7-oxide (245.4 mg) and toluene (7.9 mL) was added phosphoryl chloride (0.367 mL). The mixture was stirred at 80° C. for 3 h. After cooling, the mixture was concentrated. The residue was neutralized with saturated aqueous NaHCO3 and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (147 mg).

Workup

temperatureAfter cooling
concentrationthe mixture was concentrated
extractionextracted with EtOAc
washThe organic layer was washed with 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-6053eadebabe47829b2be75c340ab3dc
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238639B2

Reaction notes

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