Potassium Carbonate → Methyl 3-[2-(3-fluorobenzyloxy)-3'-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoate

HRID 250903Notes

Reaction equation

HRID 250903 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]Br.[CH2:10]([NH:17][C:18](=[O:40])[N:19]([C:21]1[CH:22]=[C:23]([C:27]2[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][C:35]([O:37][CH3:38])=[O:36])=[CH:29][C:28]=2[OH:39])[CH:24]=[CH:25][CH:26]=1)[CH3:20])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][O:39][C:28]1[CH:29]=[C:30]([CH2:33][CH2:34][C:35]([O:37][CH3:38])=[O:36])[CH:31]=[CH:32][C:27]=1[C:23]1[CH:24]=[CH:25][CH:26]=[C:21]([N:19]([CH3:20])[C:18]([NH:17][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:40])[CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 680073-Fluorobenzyl bromideHCID 11582687Methyl 3-[3'-(3-heptyl-1-methylureido)-2-hydroxybiphenyl-4-yl]propanoate

Product 1

HCID 67272312Methyl 3-[2-(3-fluorobenzyloxy)-3'-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

In a manner similar to that of Example (25a), by reaction of 300 μL (2.4 mmol, 2.6 eq) of 3-fluorobenzyl bromide and 400 mg (0.93 mmol, 1 eq) of methyl 3-[3′-(3-heptyl-1-methylureido)-2-hydroxybiphenyl-4-yl]propanoate (prepared in Example 15f) in 10 ml of methyl ethyl ketone in the presence of 500 mg (3.61 mmol, 3.9 eq) of potassium carbonate at 90° C. for 3 hours, methyl 3-[2-(3-fluorobenzyloxy)-3′-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoate is obtained in oil form and is used in the following reaction without further purification.

Sources & evidence

ORD record
ord-a618e0a4b64d4a5c9b49dafead9d8781
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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