Potassium Phosphate, Tribasic → tert-butyl 5-(1-methyl-1H-pyrazol-4-yl)-pyridine-2-carboxylate

HRID 1842150Notes

Reaction equation

HRID 1842150 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5](B2OC(C)(C)C(C)(C)O2)[CH:4]=[N:3]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[C:25]1[CH:26]=[CH:27][C:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[N:29][CH:30]=1>O1CCOCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH3:1][N:2]1[CH:6]=[C:5]([C:25]2[CH:26]=[CH:27][C:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[N:29][CH:30]=2)[CH:4]=[N:3]1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 24997839tert-Butyl 5-bromopyridine-2-carboxylate

Product 1

HCID 57827379tert-butyl 5-(1-methyl-1H-pyrazol-4-yl)-pyridine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (80.7 mg), bis(tri-tert-butylphosphine)palladium (0) (9.91 mg) and a 1 N potassium phosphate solution (388 μL) were added to a solution of tert-butyl 5-bromopyridine-2-carboxylate (50 mg) in 1,4-dioxane (2 mL). After replacement with nitrogen, the mixture was heated to 100° C. and stirred for eight hours. The reaction solution was cooled to room temperature, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound as a mixture (81 mg).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9fbfa127ecac4288add9f97d2dd37027
Source dataset
uspto-grants-2015_02
Patent number
US08946211B2

Reaction notes

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