Cesium fluoride → Ethyl 3-(4-chlorophenylamino)-3-oxo-2,2-diphenylpropanoate

HRID 2172655Notes

Reaction equation

HRID 2172655 reaction equation
[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]#1.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:22])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:10][CH:9]=1.C([O-])(O)=O.[Na+].[F-].[Cs+]>CC#N>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15](=[O:22])[C:16]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 25953Cesium fluorideHCID 1230681,3-Cyclohexadien-5-yneHCID 516892Sodium BicarbonateHCID 1518288Ethyl 3-[(4-chlorophenyl)amino]-3-oxopropanoate

Product 1

HCID 60203753Ethyl 3-(4-chlorophenylamino)-3-oxo-2,2-diphenylpropanoateYield 65%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
30 °C

Procedure

To the stirred solution of benzyne precursor 1 (100 mg, 0.33 mmol) and malonamide ester 2 (40 mg, 0.16 mmol) in anhydrous MeCN (2 mL) was added NaHCO3 (28 mg, 0.33 mmol), CsF (200 mg, 1.34 mmol). Reaction mixture was allowed to stir at room temperature 30° C. for 48 hrs. The reaction mixture was concentrated in vacuo and directly loaded on silica gel and purified by using gradient solvent combination of ethyl acetate/Pet ether to yield a low melting solid compound 4 (43 mg, 65%).

Workup

  1. customReaction mixture
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompurified

Sources & evidence

ORD record
ord-9b21bbb56d83476daa16e287812b1e2e
Source dataset
uspto-grants-2015_06
Patent number
US09056817B2

Reaction notes

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