Dimethylformamide → Methyl(4-chloro-6-((1,3-dimethyl-1H-pyrazol-5-yl)methoxy)-1-benzothiophen-3-yl)acetate

HRID 591424Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[C:9]2[C:10]([Cl:15])=[CH:11][C:12]([OH:14])=[CH:13][C:8]=2[S:7][CH:6]=1.CN(C=O)C.Cl[CH2:23][C:24]1[N:28]([CH3:29])[N:27]=[C:26]([CH3:30])[CH:25]=1.C([O-])([O-])=O.[K+].[K+]>O>[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[C:9]2[C:10]([Cl:15])=[CH:11][C:12]([O:14][CH2:23][C:24]3[N:28]([CH3:29])[N:27]=[C:26]([CH3:30])[CH:25]=3)=[CH:13][C:8]=2[S:7][CH:6]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of methyl(4-chloro-6-hydroxy-1-benzothiophen-3-yl)acetate (125 mg) and DMF (dry) (2 mL) were added 5-(chloromethyl)-1,3-dimethyl-1H-pyrazole (84 mg) and K2CO3 (101 mg) at room temperature, and the mixture was stirred at 60° C. for 1 h. The mixture was poured into water at room temperature and extracted with EtOAc. The organic layer was separated, 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 (172 mg).

Workup

extractionextracted with EtOAc
customThe organic layer was separated
washwashed 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-60a83916a7354253baa9caef8528eecd
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238639B2

Reaction notes

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