N-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → methyl(E)-3-(2-butoxy-3'-methylaminobiphenyl-4-yl)acrylate

HRID 250921Notes

Reaction equation

HRID 250921 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8](/[CH:13]=[CH:14]/[C:15]([O:17][CH3:18])=[O:16])[CH:9]=[CH:10][C:11]=1I)[CH2:2][CH2:3][CH3:4].[CH3:19][NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23](B2OC(C)(C)C(C)(C)O2)[CH:22]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C)C=O>[CH2:1]([O:5][C:6]1[CH:7]=[C:8](/[CH:13]=[CH:14]/[C:15]([O:17][CH3:18])=[O:16])[CH:9]=[CH:10][C:11]=1[C:23]1[CH:24]=[CH:25][CH:26]=[C:21]([NH:20][CH3:19])[CH:22]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 57976762N-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 66591222methyl(E)-3-(3-butoxy-4-iodophenyl)acrylate

Product 1

HCID 67272862methyl(E)-3-(2-butoxy-3'-methylaminobiphenyl-4-yl)acrylateYield 86.5%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

In a manner similar to that of Example (18d), by reaction of 28 mg (1 mol %) of palladium acetate, 88 mg (2 mol %) of dicyclohexylbiphenylphosphine, 4.5 g (12.5 mmol, 1.0 eq) of methyl (E)-3-(3-butoxy-4-iodophenyl)acrylate and 3.79 g (16.2 mmol, 1.3 eq) of methyl[3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl]amine (prepared in Example 7a) in 72 mL of a mixture of dimethylformamide/2M potassium phosphate solution (5/1) at 90° C. for 2 hours, 3.67 g of methyl (E)-3-(2-butoxy-3′-methylaminobiphenyl-4-yl)acrylate are obtained in the form of crystals. Yield=86%

Sources & evidence

ORD record
ord-99d3d9edb8934daf938f7d0cb6272660
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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