Benzaldehyde → HCID 178506072, compound

HRID 409629Notes

Reaction equation

HRID 409629 reaction equation
C(O[K])(C)(C)C.[CH3:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([C:14]2[NH:18][N:17]=[C:16]([C:19]([F:22])([F:21])[F:20])[CH:15]=2)[CH:9]=1.[CH:23](=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C>[CH:7](/[C:8]1[CH:13]=[CH:12][N:11]=[C:10]([C:14]2[NH:18][N:17]=[C:16]([C:19]([F:22])([F:20])[F:21])[CH:15]=2)[CH:9]=1)=[CH:23]\[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 178418922HCID 178418922, compoundHCID 178428466HCID 178428466, compound

Product 1

HCID 178506072HCID 178506072, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ligand L1 was synthesized employing a modified literature procedure,[4] in which solid tert-BuOK (1.19 g, 10.56 mmol) was added to a solution of 4-methyl-2-(3-(trifluoromethyl)-1H-pyrazol-5-yl) pyridine (0.30 g, 1.32 mmol) and benzaldehyde (0.4 mL, 3.96 mmol) in anhydrous DMF (100 mL). The resulting mixture was stirred 6 h at 100□ under nitrogen. The solvent was then evaporated, and product was dissolved in water titrated by 2 M HCl until pH 3˜4. The insoluble solid was filtered on a sintered crucible and recrystallized from hot ethylacetate (EA), filtered, and washed with methanol to obtain the desired product L1 as a beige solid (0.22 g, 51%).

Workup

  1. customLigand L1 was synthesized
  2. customThe solvent was then evaporated
  3. dissolutionproduct was dissolved in water
  4. filtrationThe insoluble solid was filtered on a sintered crucible and
  5. customrecrystallized from hot ethylacetate (EA)
  6. filtrationfiltered
  7. washwashed with methanol

Sources & evidence

ORD record
ord-5f0694ccc48946188961dae029e98eb6
Source dataset
uspto-grants-2014_06
Patent number
US08759521B2

Reaction notes

Loading…