Water → HCID 86700752, compound

HRID 2272545Notes

Reaction equation

HRID 2272545 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH:7]([C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[N:19]2[CH:23]=[C:22]([C:24]3[CH:25]=[N:26][N:27]([CH3:29])[CH:28]=3)[N:21]=[CH:20]2)[NH:12][N:11]=1)([CH3:9])[CH3:8].[CH2:30]([C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][C:39]=1F)[C:35]#[N:36])[CH3:31].O>CS(C)=O>[CH2:30]([C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][C:39]=1[N:12]1[C:13]2[C:18](=[C:17]([N:19]3[CH:23]=[C:22]([C:24]4[CH:25]=[N:26][N:27]([CH3:29])[CH:28]=4)[N:21]=[CH:20]3)[CH:16]=[CH:15][CH:14]=2)[C:10]([CH:7]([CH3:9])[CH3:8])=[N:11]1)[C:35]#[N:36])[CH3:31]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 577184393-Ethyl-4-fluorobenzonitrileHCID 178440406HCID 178440406, compound

Product 1

HCID 86700752HCID 86700752, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
130 °C

Procedure

Cesium carbonate (850 mg) was added to a solution of compound (5a) (200 mg) in DMSO (2.2 mL), and the mixture was heated to 130° C. The mixture was stirred for 10 minutes and 3-ethyl-4-fluorobenzonitrile (292 mg) was added thereto. The resulting mixture was stirred at the same temperature for 1.5 hours. After completion of the reaction, the reaction solution was allowed to standing still for cooling, and water was poured thereto. The reaction solution was partitioned between ethyl acetate and water. The organic layer was washed with saturated brine and dried by the addition of anhydrous sodium sulfate. After removal of the solvent by evaporation, the residue was purified by neutral silica gel column chromatography (chloroform/ethyl acetate/methanol) to obtain compound (6a) (151.8 mg, yield 54%) as a white foamy substance.

Workup

  1. stirringThe resulting mixture was stirred at the same temperature for 1.5 hours
  2. customAfter completion of the reaction
  3. temperaturefor cooling
  4. customThe reaction solution was partitioned between ethyl acetate and water
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried by the addition of anhydrous sodium sulfate
  7. customAfter removal of the solvent
  8. customby evaporation
  9. customthe residue was purified by neutral silica gel column chromatography (chloroform/ethyl acetate/methanol)

Sources & evidence

ORD record
ord-519737d67aa24ea8b32b3c702b717ecf
Source dataset
uspto-grants-2015_09
Patent number
US09120780B2

Reaction notes

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