Cesium carbonate → HCID 86700750, compound

HRID 2272543Notes

Reaction equation

HRID 2272543 reaction equation
[CH:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[N:13]2[CH:17]=[C:16]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[N:15]=[CH:14]2)[NH:6][N:5]=1)([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:31]1[CH:38]=[CH:37][C:34]([C:35]#[N:36])=[C:33]([NH:39][C:40]([CH3:43])([CH3:42])[CH3:41])[CH:32]=1.CN(C)CCN>O1CCOCC1.[Cu]I>[C:40]([NH:39][C:33]1[CH:32]=[C:31]([N:6]2[C:7]3[C:12](=[C:11]([N:13]4[CH:17]=[C:16]([C:18]5[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=5)[N:15]=[CH:14]4)[CH:10]=[CH:9][CH:8]=3)[C:4]([CH:1]([CH3:3])[CH3:2])=[N:5]2)[CH:38]=[CH:37][C:34]=1[C:35]#[N:36])([CH3:43])([CH3:41])[CH3:42]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 66053N,N-DimethylethylenediamineHCID 67501505HCID 67501505, compoundHCID 178440405HCID 178440405, compound

Product 1

HCID 86700750HCID 86700750, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

A solution of compound (1a) (200 mg), copper(I) iodide (50 mg), cesium carbonate (430 mg), 4-bromo-2-(tert-butylamino)benzonitrile (250 mg), and N,N-dimethylethane-1,2-diamine (0.11 mL) in 1,4-dioxane (3.3 mL) was stirred overnight under heating at 150° C. After completion of the reaction, the reaction solution was allowed to standing still for cooling, filtered, and the filtrate 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 (1b) (146 mg, yield 47%) as a white foamy substance.

Workup

  1. customAfter completion of the reaction
  2. temperaturefor cooling
  3. filtrationfiltered
  4. customthe filtrate 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-80c288ed4dca471e9a163f8461efda98
Source dataset
uspto-grants-2015_09
Patent number
US09120780B2

Reaction notes

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