Dimethylformamide → ethyl 3-[3-ethoxy-1-[4-[3-methyl-1-(2-pyridyl)-1H-pyrazol-4-ylmethoxy]benzyl]-1H-pyrazol-4-yl]propionate

HRID 350252Notes

Reaction equation

Cl[CH2:2][C:3]1[C:4]([CH3:14])=[N:5][N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:7]=1.[CH2:15]([O:17][C:18]1[C:22]([CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:21][N:20]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=2)[N:19]=1)[CH3:16].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:15]([O:17][C:18]1[C:22]([CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:21][N:20]([CH2:30][C:31]2[CH:32]=[CH:33][C:34]([O:37][CH2:2][C:3]3[C:4]([CH3:14])=[N:5][N:6]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=4)[CH:7]=3)=[CH:35][CH:36]=2)[N:19]=1)[CH3:16]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-(4-chloromethyl-3-methyl-1H-pyrazol-1-yl)pyridine (350 mg), ethyl 3-[3-ethoxy-1-(4-hydroxybenzyl)-1H-pyrazol-4-yl]propionate (500 mg), potassium carbonate (500 mg) and N,N-dimethylformamide (10 ml) was stirred at 80° C. for 5 hours. The reaction mixture was poured into water, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography to obtain ethyl 3-[3-ethoxy-1-[4-[3-methyl-1-(2-pyridyl)-1H-pyrazol-4-ylmethoxy]benzyl]-1H-pyrazol-4-yl]propionate (700 mg, yield: 91%) as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (1:2, volume ratio).

Workup

extractionextracted with ethyl acetate
washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
dry with materialdried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-abff32d53790472facecc7a1c4c9cb59
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07179823B1

Reaction notes

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