Toluene → HCID 54428531, compound

HRID 1178866Notes

Reaction equation

HRID 1178866 reaction equation
[O:1]([C:3](C)(C)C)[Na].[NH2:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[CH2:13])=[CH:10][CH:9]=1.I[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1.[C:25]1(C)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C[CH2:33][O:34][C:35]([CH3:37])=O.[CH3:38][CH2:39][CH2:40][CH2:41]CC>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]>[CH3:24][O:23][C:20]1[CH:21]=[CH:22][C:17]([N:7]([C:28]2[CH:27]=[CH:26][C:25]([O:1][CH3:3])=[CH:30][CH:29]=2)[C:8]2[CH:15]=[CH:14][C:11]([CH:12]=[CH:13][C:40]3[CH:41]=[CH:37][C:35]([O:34][CH3:33])=[CH:38][CH:39]=3)=[CH:10][CH:9]=2)=[CH:18][CH:19]=1

Participants

7

Reactant 5

HCID 1140TolueneHCID 696764-IodoanisoleHCID 737004-AminostyreneHCID 21226206Ethyl acetate hexaneHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 54428531HCID 54428531, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Following the general procedure, Pd2dba3 (18.3 mg, 2 mol %), NaO-t-Bu (336 mg, 3.5 mmol), P(isoBuNCH2CH2)3N (13.6 mg, 4 mol %), 4-aminostyrene (119 mg, 1 mmol), 4-iodoanisole (749 mg, 3.2 mmol), and 10 mL of dry toluene at 110° C. for 16 h produced (5) N,N-bis(4-methoxyphenyl)-4-[2-(4-methoxyphenyl) ethenyl]benzenamine (180 mg, 41%) as the sole product after chromatography with 1-5% EtOAc/hexane mixture. (See Entry 8 of Table 2).

Workup

  1. customat 110° C.
  2. customfor 16 h

Sources & evidence

ORD record
ord-86b206daa0734358a2d57d5f3ee117bf
Source dataset
uspto-grants-2007_10
Patent number
US07276627B2

Reaction notes

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