Cesium carbonate → 2-{4-[3-(3,4-Dichlorophenyl)-propyl]phenylamino}benzoic acid methyl ester

HRID 488501Notes

Reaction equation

HRID 488501 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:19][O:20][C:21](=[O:29])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=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>[CH3:19][O:20][C:21](=[O:29])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][CH2:10][CH2:9][C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)=[CH:17][CH:16]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 11894Methyl 2-bromobenzoateHCID 222697484-[3-(3,4-Dichloro-phenyl)propyl]phenylamine

Product 1

HCID 545136252-{4-[3-(3,4-Dichlorophenyl)-propyl]phenylamino}benzoic acid methyl esterYield 82.6%

Reagents, catalysts & solvents 3

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

Procedure

The title compound was prepared from 4-[3-(3,4-dichlorophenyl)propyl]-phenylamine (600 mg, 2.14 mmol), 2-bromobenzoic acid methyl ester (380 mg, 1.78 mmol), cesium carbonate (812 mg, 2.49 mmol), tris(dibenzylideneacetone-dipaladium(0) (49 mg, 0.053 mmol) and (S)-2,2′-bis(di-p-tolylphosphino-1,1′-binaphthyl (98%, (S)-tol-BINAP) (54 mg, 0.080 mmol) (Ligand/Pd=1.5) in anhydrous toluene (15 mL) using the procedure described in Example 2, Step C. This procedure yielded an yellow oil, 0.61 g (1.47 mmol, 69%) of the desired product.

Sources & evidence

ORD record
ord-367032a5e3bc4740b90d24e15c1f2351
Source dataset
uspto-grants-2005_12
Patent number
US06972287B1

Reaction notes

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