Cesium carbonate → HCID 71295167, compound

HRID 868827Notes

Reaction equation

HRID 868827 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:7][O:8][CH2:9][CH2:10]Br.[CH:12]1([CH2:15][O:16][C:17]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][N:28]=[C:27]([NH:31][C:32]4[CH:33]=[N:34][NH:35][CH:36]=4)[CH:26]=3)=[CH:21][C:18]=2[C:19]#[N:20])[CH2:14][CH2:13]1>CN(C=O)C>[CH:12]1([CH2:15][O:16][C:17]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][N:28]=[C:27]([NH:31][C:32]4[CH:33]=[N:34][N:35]([CH2:10][CH2:9][O:8][CH3:7])[CH:36]=4)[CH:26]=3)=[CH:21][C:18]=2[C:19]#[N:20])[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 809722-Bromoethyl methyl etherHCID 71295244HCID 71295244, compound

Product 1

HCID 71295167HCID 71295167, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Caesium carbonate (0.17 g, 0.54 mmol) and 2-bromoethyl methyl ether (0.045 g, 0.325 mmol) are added to a solution of the 2-cyclopropylmethoxy-5-[2-(1H-pyrazol-4-ylamino)pyridin-4-yl]benzonitrile prepared above (0.09 g, 0.27 mmol) in dry DMF (2 ml). The reaction mixture is warmed at 80° C. for 8 h. Ice is added, and the mixture is extracted with ethyl acetate (2×50 ml). The organic phase is washed with water (1×25 ml) and dried over sodium sulfate. The mixture is then evaporated in a rotary evaporator. The crude product is purified by chromatography, giving 5.8 mg of the desired product as brown solid;

Workup

  1. additionIce is added
  2. extractionthe mixture is extracted with ethyl acetate (2×50 ml)
  3. washThe organic phase is washed with water (1×25 ml)
  4. dry with materialdried over sodium sulfate
  5. customThe mixture is then evaporated in a rotary evaporator
  6. customThe crude product is purified by chromatography

Sources & evidence

ORD record
ord-51dc5c37991b47c599d782b598a18632
Source dataset
uspto-grants-2015_03
Patent number
US08969335B2

Reaction notes

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