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

HRID 2172654Notes

Reaction equation

HRID 2172654 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][CH:3]=1.[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]#1.[F-].[Cs+]>CC#N>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:16])[C:10]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:7]=1

Participants

5

Reactant 3

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

Product 1

HCID 60203753Ethyl 3-(4-chlorophenylamino)-3-oxo-2,2-diphenylpropanoateYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The present invention further provides one pot process for C-arylation of ethyl 3-(4-chlorophenylamino)-3-oxo-propanoate (2) using benzyne precursor (1) in presence of CsF and CH3CN to obtain ethyl 3-(4-chlorophenylamino)-3-oxo-2,2-diphenylpropanoate (4) with more than 85% yield (cf scheme 3).

Sources & evidence

ORD record
ord-3ea9f64ad1e84360adc179645af81a90
Source dataset
uspto-grants-2015_06
Patent number
US09056817B2

Reaction notes

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