Potassium Carbonate → Methyl 4'-[(3-butyl-1,4-dihydro-4-oxo-1-quinolinyl)-methyl](1,1'-biphenyl)-2-carboxylate

HRID 1602934Notes

Reaction equation

[CH2:1]([C:5]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[C:16](=O)([O-])[O-].[K+].[K+].BrC[C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:25]=1[C:36]([O:38][CH3:39])=[O:37]>>[CH2:1]([C:5]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:16][C:33]2[CH:32]=[CH:31][C:30]([C:26]3[C:25]([C:36]([O:38][CH3:39])=[O:37])=[CH:24][CH:29]=[CH:28][CH:27]=3)=[CH:35][CH:34]=2)[CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 195953413-butyl-4-(1H)-quinolinone

HCID 19608489Methyl bromomethyl-(1,1'-biphenyl)-2-carboxylate

Product 1

HCID 19608515Methyl 4'-[(3-butyl-1,4-dihydro-4-oxo-1-quinolinyl)-methyl](1,1'-biphenyl)-2-carboxylateYield 94.1%

Procedure

Using the procedure of Example 1, 4.02 g of the compound of Step E of Example 1 and 5.52 g of potassium carbonate and 6.2 g of methyl bromomethyl-(1,1'biphenyl)-2-carboxylate (preparation according to EP 0,253,310) were reacted to obtain after chromatography on silica (eluant: methylene chloride-methanol (98-2)), 8 g of the desired product.

Workup

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Sources & evidence

ORD record: ord-e09bfba82b844c2986b63b2947192b55
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05985894

Reaction notes

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