Cesium carbonate → HCID 57520172, compound

HRID 1528102Notes

Reaction equation

HRID 1528102 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[N:13]=[CH:12][CH:11]=[C:10]3[NH:17][C:18]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[N:22]=2)=[O:19])[CH2:3][CH2:2]1.Br[CH2:32][CH2:33][F:34].C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)(O)[O-].[Na+]>O1CCOCC1>[F:34][CH2:33][CH2:32][N:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[N:13]=[CH:12][CH:11]=[C:10]3[NH:17][C:18]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:28])([F:29])[F:30])[N:22]=2)=[O:19])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 129822-Fluoroethyl bromide2×HCID 516892Sodium BicarbonateHCID 57520095HCID 57520095, compound

Product 1

HCID 57520172HCID 57520172, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

The reaction mixture containing 0.27 g of 1-(6-(piperidin-4-yl)quinolin-4-yl)-3-(6-(trifluoromethyl)pyridin-2-yl)urea (0.650 mmol), 0.073 ml of 1-bromo-2-fluoroethane (0.975 mmol), 1.059 g of cesium carbonate (3.25 mmol) and 6.5 of dioxane was shaken in a flask at 60° C. for 4 h. Due to non complete reaction, additional 0.049 ml of 1-bromo-2-fluoroethane (0.650 mmol) were added and the reaction mixture was shaken at 60° C. for 18 h. Saturated sodium bicarbonate solution was added and the mixture extracted three times with ethyl acetate. The combined organic phases were washed once with brine, dried over sodiumsulfat and the solvent removed under reduced pressure. After purifying of the raw material (190 mg) by column chromatography (silica gel, DCM/MeOH 95:5) 90 mg of the desired product were obtained as beige powder (yield: 30%).

Workup

  1. additionwere added
  2. stirringthe reaction mixture was shaken at 60° C. for 18 h
  3. extractionthe mixture extracted three times with ethyl acetate
  4. washThe combined organic phases were washed once with brine
  5. dry with materialdried over sodiumsulfat
  6. customthe solvent removed under reduced pressure
  7. customAfter purifying of the raw material (190 mg) by column chromatography (silica gel, DCM/MeOH 95:5) 90 mg of the desired product

Sources & evidence

ORD record
ord-e719c958e65140f394d236df1ff38a7e
Source dataset
uspto-grants-2015_07
Patent number
US09090592B2

Reaction notes

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