Sodium Iodide → Methyl 3-[2-(2-ethoxyethoxy)-3'-(1-methyl-3-pentylureido)biphenyl-4-yl]propanoate

HRID 250923Notes

Reaction equation

HRID 250923 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5]Br)[CH3:2].[OH:7][C:8]1[CH:13]=[C:12]([CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:11]=[CH:10][C:9]=1[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([N:26]([CH3:35])[C:27]([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[O:28])[CH:21]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(C(C)=O)C>[CH2:1]([O:3][CH2:4][CH2:5][O:7][C:8]1[CH:13]=[C:12]([CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:11]=[CH:10][C:9]=1[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([N:26]([CH3:35])[C:27]([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[O:28])[CH:21]=1)[CH3:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 611412-Bromoethyl ethyl etherHCID 67273049HCID 67273049, compound

Product 1

HCID 67272882Methyl 3-[2-(2-ethoxyethoxy)-3'-(1-methyl-3-pentylureido)biphenyl-4-yl]propanoateYield 96%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

In a manner similar to that of Example (25a), by reaction of 230 mg (1 mmol, 1.5 eq) of 2-bromoethyl ethyl ether and 400 mg (1.0 mmol, 1 eq) of methyl 3-[2-hydroxy-3′-(1-methyl-3-pentylureido)biphenyl-4-yl]propanoate (prepared as in Example 46d) in 10 ml of methyl ethyl ketone in the presence of 415 mg (3.0 mmol, 3 eq) of potassium carbonate and 60 mg (0.4 mmol, 0.4 eq) of sodium iodide at 90° C. for 48 hours, 450 mg of methyl 3-[2-(2-ethoxyethoxy)-3′-(1-methyl-3-pentylureido)biphenyl-4-yl]propanoate are obtained in the form of a yellow oil. Yield=96%

Sources & evidence

ORD record
ord-d284582618ca4af5aa847c6256da423d
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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