Cesium carbonate → HCID 66957699, compound

HRID 1192788Notes

Reaction equation

HRID 1192788 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=2)=[N:2]1.Br[C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:24])[CH2:22][CH3:23])=[CH:17][CH:16]=1.C([O-])([O-])=O.[Cs+].[Cs+]>[Cu]I.OC1C=CC=C2C=1N=CC=C2.CN(C=O)C.O>[C:21]([C:18]1[CH:19]=[CH:20][C:15]([N:1]2[CH:5]=[CH:4][C:3]([C:6]3[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=3)=[N:2]2)=[CH:16][CH:17]=1)(=[O:24])[CH2:22][CH3:23]

Participants

7

Reactant 3

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

Product 1

HCID 66957699HCID 66957699, 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-(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%). Reduction of the nitrile to the corresponding aldehyde was accomplished following the DIBAL procedure described earlier.

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-b580f3ee7d16412584f56c28150e8ea1
Source dataset
uspto-grants-2014_03
Patent number
US08680269B2

Reaction notes

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