Cesium carbonate → 2-{4-[2-(3,4-Dimethyl-phenyl)-ethyl]phenylamino)-5-nitrobenzoic acid methyl ester

HRID 488515Notes

Reaction equation

HRID 488515 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].[CH3:18][O:19][C:20](=[O:31])[C:21]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23][C:22]=1Br.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.[Pd].C1(C)C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2)C2C=CC(C)=CC=2)=CC=1>[CH3:18][O:19][C:20](=[O:31])[C:21]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23][C:22]=1[NH:17][C:14]1[CH:13]=[CH:12][C:11]([CH2:10][CH2:9][C:4]2[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=2)=[CH:16][CH:15]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 245494Methyl 2-Bromo-5-nitrobenzoateHCID 145552094-[2-(3,4-Dimethylphenyl)ethyl]-benzenamine

Product 1

HCID 541399142-{4-[2-(3,4-Dimethyl-phenyl)-ethyl]phenylamino)-5-nitrobenzoic acid methyl esterYield 87.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 18398271Di-p-tolylphosphino-1,1'-binaphthylCatalystHCID 1140TolueneSolvent

Procedure

The title compound was prepared from 4-[2-(3,4-dimethylphenyl)ethyl]-benzenamine (1.0 g, 4.43 mmol), 2-bromo-5-nitrobenzoic acid methyl ester (0.96 g, 3.69 mmol), cesium carbonate (1.68 g, 5.17 mmol), tris(dibenzylideneacetone-dipaladium(0) (101 mg, 0.11 mmol) and (S)-(2,2′-bis(di-p-tolylphosphino-1,1′-binaphthyl (98%, (S)-tol-BINAP) (113 mg, 0.17 mmol) (Ligand/Pd=1.5) in anhydrous toluene (32 mL) using the procedure described in Example 2, step C. This procedure yielded an yellow solid, 1.31 g (3.24 mmol, 73%) of the desired product. mp 115-117° C.

Sources & evidence

ORD record
ord-29762f8125c9414e9b2f781c10b073b5
Source dataset
uspto-grants-2005_12
Patent number
US06972287B1

Reaction notes

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