Sodium Carbonate → HCID 66995153, compound

HRID 2066419Notes

Reaction equation

HRID 2066419 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](I)=[N:7][N:8]2[CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])=[CH:4][CH:3]=1.[CH3:20][N:21]1[CH:25]=[C:24](B2OC(C)(C)C(C)(C)O2)[CH:23]=[N:22]1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.O.[Cl-].[Na+].O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:24]3[CH:23]=[N:22][N:21]([CH3:20])[CH:25]=3)=[N:7][N:8]2[CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])=[CH:4][CH:3]=1

Participants

9

Reactant 3

HCID 10340Sodium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 58515210HCID 58515210, compound

Product 1

HCID 66995153HCID 66995153, compound

Reagents, catalysts & solvents 5

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of Example 1B (0.500 g, 1.103 mmol) and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.275 g, 1.324 mmol) in toluene (8 ml) and ethanol (8 ml) under argon was treated with an aqueous solution of sodium carbonate (0.292 g, 2.76 mmol) in water (2 ml). Added Pd(PPh3)4(0.217 g, 0.188 mmol) and the resulting heterogeneous mixture was refluxed at 80° C. for 2 hours, then stirred at room temperature for 18 hours. The reaction mixture was diluted with brine and extracted twice with ethyl acetate. The combined organics were dried with MgSO4, concentrated and the residue purified via silica gel chromatography eluting with 0.5% methanol in CH2Cl2 to afford the title compound.

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe combined organics were dried with MgSO4
  3. concentrationconcentrated
  4. customthe residue purified via silica gel chromatography
  5. washeluting with 0.5% methanol in CH2Cl2

Sources & evidence

ORD record
ord-085af2d588564e768867ae2f52ba4e01
Source dataset
uspto-grants-2012_10
Patent number
US08293738B2

Reaction notes

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