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

HRID 591396
Notes
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Reaction equation

HRID 591396 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[C:9]2[C:10]([CH3:15])=[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]([CH3:15])=[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 49612705-(chloromethyl)-1,3-dimethyl-1H-pyrazoleHCID 121001301Methyl(6-hydroxy-4-methyl-1-benzothiophen-3-yl)acetate

Product 1

HCID 118667002Methyl(6-((1,3-dimethyl-1H-pyrazol-5-yl)methoxy)-4-methyl-1-benzothiophen-3-yl)acetateYield 70.9%

Reagents, catalysts & solvents

1
HCID 962WaterSolvent

Procedure

To a mixture of methyl(6-hydroxy-4-methyl-1-benzothiophen-3-yl)acetate (150 mg) and DMF (2 mL) were added 5-(chloromethyl)-1,3-dimethyl-1H-pyrazole (101 mg) and K2CO3 (175 mg) at room temperature. The mixture was stirred at room temperature for 3 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). The product was crystallized from Et2O-hexane to give the title compound (155 mg).

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed successively with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)
  7. customThe product was crystallized from Et2O-hexane

Sources & evidence

ORD record
ord-c12b281d243d4a5d9ca264a03db09543
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09238639B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes