Cesium carbonate → HCID 89647623, compound

HRID 2274605Notes

Reaction equation

HRID 2274605 reaction equation
[CH2:1]([N:5]([CH2:14][CH2:15][CH2:16][CH3:17])[C:6]([C:8]1[CH:12]=[C:11]([CH3:13])[NH:10][N:9]=1)=[O:7])[CH2:2][CH2:3][CH3:4].I[C:19]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:20]=1[C:21]([OH:23])=[O:22].C(=O)([O-])[O-].[Cs+].[Cs+].CO.C(Cl)Cl>O1CCOCC1.C(OCC)(=O)C.[Cu](I)I>[CH2:1]([N:5]([CH2:14][CH2:15][CH2:16][CH3:17])[C:6]([C:8]1[CH:12]=[C:11]([CH3:13])[N:10]([C:19]2[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:20]=2[C:21]([OH:23])=[O:22])[N:9]=1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 128221822-Iodo-4-methoxybenzoic acidHCID 21226129Dichloromethane methanolHCID 89649710HCID 89649710, compound

Product 1

HCID 89647623HCID 89647623, compoundYield 31%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-methyl-1H-pyrazole-3-carboxylic acid dibutylamide (0.85 g, 3.6 mmol), 2-iodo-4-methoxybenzoic acid (1.0 g, 3.6 mmol), copper iodide (0.14 g, 0.72 mmol), cesium carbonate (1.2 g, 3.6 mmol), and trans-dimethylaminecyclohexane (0.23 mL, 1.44 mmol) in dioxane (5 mL) was microwaved at 120° C. for 15 minutes. Diluted with ethyl acetate, the crude material was eluted through a silica gel column with a 0 to 100% ethyl acetate/heptane and then 0 to 20% methanol/methylene chloride gradient to afford the title compound (0.43 g, 31% yield). MS (ESI) [m/e, (M+H)+]=388.5.

Workup

  1. customwas microwaved at 120° C. for 15 minutes
  2. washthe crude material was eluted through a silica gel column with a 0 to 100% ethyl acetate/heptane

Sources & evidence

ORD record
ord-707caa612eb64a3e8987931718bce632
Source dataset
uspto-grants-2015_09
Patent number
US09126979B2

Reaction notes

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