Cesium carbonate → HCID 66969077, compound

HRID 1189496Notes

Reaction equation

HRID 1189496 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[CH:14][C:13]([C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=3)=[N:12]2)=[CH:7][CH:6]=1)(=[O:4])[CH2:2][CH3:3].N1C=CC(C2C=CC(C#N)=CC=2)=N1.BrC1C=CC(C(=O)CC)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>[Cu]I.OC1C=CC=C2C=1N=CC=C2.CN(C=O)C.O>[OH:4][CH:1]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH:15]=[CH:14][C:13]([C:16]3[CH:17]=[CH:18][C:19]([C:20]#[N:21])=[CH:22][CH:23]=3)=[N:12]2)=[CH:9][CH:10]=1)[CH2:2][CH3:3]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 66312p-BromopropiophenoneHCID 66957699HCID 66957699, compoundHCID 178509584HCID 178509584, compound

Product 1

HCID 66969077HCID 66969077, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 19238-HydroxyquinolineCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

4-[1-(4-Propionyl-phenyl)-1H-pyrazol-3-yl]-benzonitrile. 4-(1H-Pyrazol-3-yl)-benzonitrile (100 mg, 0.591 mmol), 1-(4-bromophenyl)-propan-1-one (126 mg, 0.591 mmol), Cs2CO3 (770 mg, 2.364 mmol), CuI (4 mg, 0.018 mmol), 8-hydroxyquinoline (3 mg, 0.018 mmol), and DMF/H2O (2 mL; 10:1 solution) were combined in a 10 mL CEM Microwave reaction vessel fitted with magnetic stir bar and subjected to microwave irradiation at 150° C. for 30 min. The contents were then filtered and concentrated to dryness affording the nitrile (158 mg, 0.508 mmol, 86%).

Workup

  1. customfitted with magnetic stir bar
  2. customirradiation at 150° C. for 30 min
  3. filtrationThe contents were then filtered
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-f8a66b91ceb446dfa7104d657c5420dd
Source dataset
uspto-grants-2014_03
Patent number
US08674109B2

Reaction notes

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