2-Fluoroethylamine → 2-methylpropan-2-yl 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-[(2-fluoroethyl)amino]benzoate

HRID 1877518Notes

Reaction equation

HRID 1877518 reaction equation
C(=O)([O-])[O-].[K+].[K+].[F:7][CH2:8][CH2:9][NH2:10].[C:11]([C:13]1[N:18]=[CH:17][C:16]([C:19]2[C:31]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]([C:32]4[CH:44]=[CH:43][C:35]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[C:34](F)[CH:33]=4)[C:23]=3[CH:22]=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)#[N:12]>CS(C)=O.O>[C:11]([C:13]1[N:18]=[CH:17][C:16]([C:19]2[C:31]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]([C:32]4[CH:33]=[CH:34][C:35]([C:36]([O:38][C:39]([CH3:40])([CH3:41])[CH3:42])=[O:37])=[C:43]([NH:10][CH2:9][CH2:8][F:7])[CH:44]=4)[C:23]=3[CH:22]=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)#[N:12]

Participants

6

Reactant 3

HCID 99962-FluoroethylamineHCID 11430Potassium CarbonateHCID 583382932-methylpropan-2-yl 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-fluorobenzoate

Product 1

HCID 866551662-methylpropan-2-yl 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-[(2-fluoroethyl)amino]benzoateYield 19.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

4.83 g of potassium carbonate and 3 g (40 mmol) of 2-fluoroethylamine are successively added to a solution of 0.7 g of 2-methylpropan-2-yl 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-fluorobenzoate, obtained in stage 1 of Example 49, in 5 ml of dimethyl sulphoxide. The reaction mixture is heated at 90° C. for 2 hours and 50 minutes in a microwave, and then diluted with distilled water. The aqueous phase is washed twice with ethyl acetate and the combined organic phases are washed with water and a saturated solution of sodium chloride, dried over magnesium sulphate and concentrated to dryness under reduced pressure. The residue is purified by silica gel chromatography, elution being carried out with dichloromethane, so as to give 0.15 g of 2-methylpropan-2-yl 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-[(2-fluoroethyl)amino]benzoate in the form of a white powder, the characteristics of which are the following:

Workup

  1. washThe aqueous phase is washed twice with ethyl acetate
  2. washthe combined organic phases are washed with water
  3. dry with materiala saturated solution of sodium chloride, dried over magnesium sulphate
  4. concentrationconcentrated to dryness under reduced pressure
  5. customThe residue is purified by silica gel chromatography, elution

Sources & evidence

ORD record
ord-fce5218875df45e6af178ccedc2fdd29
Source dataset
uspto-grants-2012_11
Patent number
US08309721B2

Reaction notes

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