Iodobenzene → 3-[4-(4-Phenylamino-phenyl)-piperazin-1-yl]-propionic acid methyl ester

HRID 2353226Notes

Reaction equation

HRID 2353226 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1.I[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.O(C(C)(C)C)[Na]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:1][O:2][C:3](=[O:19])[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1

Participants

7

Reactant 4

HCID 11575IodobenzeneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 58902522Methyl 3-[4-(4-aminophenyl)piperazin-1-yl]propanoateHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 249362433-[4-(4-Phenylamino-phenyl)-piperazin-1-yl]-propionic acid methyl esterYield 11.9%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

The compound from step 2 (554 mg, 2.11 mmol) and iodobenzene (430 mg, 2.11 mmol) were dissolved in toluene (15 ml) and the following reagents were added: Pd2(dba)3 (58 mg, 0.063 mmol), PtBu3 (128 mg. 0.63 mmol) and NaO-t-Bu (202 mg, 2.11 mmol). The reaction mixture was stirred at ambient temperature overnight and then filtered. The filtrate was loaded onto a silica gel column and eluted with 1% MeOH in CH2Cl2 to yield the title compound as a yellow solid (85 mg, 11.9%): MS (ESI) m/z 340 (M+H); 1H NMR (400 MHz, CDCl3) δ 2.56 (t, J=7.2 Hz, 2H), 2.64 (t, J=4.8 Hz, 4H), 2.77 (t, J=7.2 Hz, 2H), 3.13 (br, 4H), 3.69 (s, 3H), 6.82-7.21 (m, 9H).

Workup

  1. additionthe following reagents were added
  2. filtrationfiltered
  3. washeluted with 1% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-a0356762a638420389518de96bf6bccb
Source dataset
uspto-grants-2010_07
Patent number
US07750012B2

Reaction notes

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