Cesium carbonate → HCID 68182358, compound

HRID 524398Notes

Reaction equation

HRID 524398 reaction equation
[N+:1]([C:4]1[CH:8]=[CH:7][NH:6][N:5]=1)([O-:3])=[O:2].Cl[C:10]1[N:15]=[CH:14][C:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[N+:1]([C:4]1[CH:8]=[CH:7][N:6]([C:10]2[N:15]=[CH:14][C:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:12][CH:11]=2)[N:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11521348Tert-butyl 6-chloropyridine-3-carboxylateHCID 178526745HCID 178526745, compound

Product 1

HCID 68182358HCID 68182358, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-Nitro-1H-pyrazole (0.265 gm, 2.34 mmol), tert-butyl 6-chloropyridine-3-carboxylate (0.500 gm, 2.34 mmol) was dissolved in anhydrous DMF (10 mL). Cesium carbonate (1.90 gm, 5.86 mmol) was added and reaction mixture was heated at 100° C. for 6 h. The reaction mixture was cooled to room temperature and poured into ice water, a white precipitate formed was filtered and dried under vacuum to give tert-butyl 6-(3-nitropyrazol-1-yl)pyridine-3-carboxylate (0.505 gm).

Workup

  1. customreaction mixture
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customa white precipitate formed
  4. filtrationwas filtered
  5. customdried under vacuum

Sources & evidence

ORD record
ord-962b95ec0530472e9e705e6a991cd6c0
Source dataset
uspto-grants-2016_05
Patent number
US09340506B2

Reaction notes

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