Sodium Carbonate → HCID 86683859, compound

HRID 2406711Notes

Reaction equation

HRID 2406711 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].CC1(C)C(C)(C)OB([C:15]2[CH:16]=[N:17][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:19]=2)O1.Br[C:29]1[CH:30]=[C:31]([NH2:35])[CH:32]=[N:33][CH:34]=1>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.O.O1CCCC1>[C:23]([O:22][C:20]([N:18]1[CH:19]=[C:15]([C:29]2[CH:34]=[N:33][CH:32]=[C:31]([NH2:35])[CH:30]=2)[CH:16]=[N:17]1)=[O:21])([CH3:24])([CH3:25])[CH3:26]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 8176813-Amino-5-bromopyridineHCID 16217654tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate

Product 1

HCID 86683859HCID 86683859, compoundYield 34.6%

Reagents, catalysts & solvents 3

HCID 178418851HCID 178418851, compoundCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Water (0.5 ml), sodium carbonate (92 mg), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-carboxylate (203 mg), and bis(tri-tert-butylphosphine)palladium (30 mg) were added to a tetrahydrofuran (4.5 ml) solution containing 5-bromopyridin-3-amine (100 mg) in a nitrogen atmosphere, followed by stirring for 2.75 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline and dried over anhydrous sodium sulfate. Subsequently, the solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (chloroform:methanol=1:0 to 30:1), and a white solid of tert-butyl-4-(5-aminopyridin-3-yl)-1H-pyrazol-1-carboxylate (52 mg) was thus obtained.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationSubsequently, the solvent was distilled away under reduced pressure
  5. customthe obtained residue was purified by silica gel chromatography (chloroform:methanol=1:0 to 30:1)

Sources & evidence

ORD record
ord-3db6c28e8ecb48429569f8a7a9c479b9
Source dataset
uspto-grants-2014_08
Patent number
US08809371B2

Reaction notes

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