Cesium carbonate → HCID 57364150, compound

HRID 2426993Notes

Reaction equation

HRID 2426993 reaction equation
Br[C:2]1[CH:25]=[CH:24][C:5]([C:6]([N:19]2[CH:23]=[CH:22][CH:21]=[N:20]2)([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[F:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[F:26][C:27]1[CH:32]=[CH:31][C:30]([C:22]2[CH:21]=[N:20][N:19]([C:6]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:5]3[CH:24]=[CH:25][CH:2]=[CH:3][CH:4]=3)[CH:23]=2)=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 2856454-Fluorophenylboronic acidHCID 67148464HCID 67148464, compound

Product 1

HCID 57364150HCID 57364150, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-bromo-trityl-1H-pyrazole (0.7 g) in N,N-dimethylformamide (14 ml) was added 4-fluorophenylboronic acid (0.377 g), cesium carbonate (1.758 g), and tetrakis triphenylphosphine palladium (0.208 g). The resulting suspension was stirred at room temperature for 10 min. The irradiation of microwaves at 160° C. for 10 min was sufficient to complete a reaction in the suspension. The product was filtered through silica gel, diluted in ethyl acetate (30 ml) and washed with saturated ammonium chloride solution (30 ml) and then with brine (30 ml). The washed organic layer thus formed was dried over anhydrous magnesium sulfate and concentrated by evaporation in a vacuum. The residue thus obtained was separated using silica gel chromatography to produce 4-(4-fluorophenyl)-1-trityl-1H-pyrazole (yield 51%).

Workup

  1. customThe irradiation of microwaves at 160° C. for 10 min
  2. customa reaction in the suspension
  3. filtrationThe product was filtered through silica gel
  4. additiondiluted in ethyl acetate (30 ml)
  5. washwashed with saturated ammonium chloride solution (30 ml)
  6. customThe washed organic layer thus formed
  7. dry with materialwas dried over anhydrous magnesium sulfate
  8. concentrationconcentrated by evaporation in a vacuum
  9. customThe residue thus obtained
  10. customwas separated

Sources & evidence

ORD record
ord-e19db34ea20b4846acbed09a87c156a5
Source dataset
uspto-grants-2011_06
Patent number
US07968579B2

Reaction notes

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