N-(3-Methylphenyl)aniline → HCID 58028469, compound

HRID 42385Notes

Reaction equation

HRID 42385 reaction equation
[C:1]12[CH2:8][CH2:7][C:6]=1[CH:5]=[CH:4][C:3]([CH2:9][CH2:10][CH2:11][CH2:12][C:13]1([CH2:28][CH2:29][CH2:30][CH2:31][C:32]3[CH:33]=[C:34]4[C:37](=[CH:38][CH:39]=3)[CH2:36][CH2:35]4)[C:25]3[CH:24]=[C:23](Br)[CH:22]=[CH:21][C:20]=3[C:19]3[C:14]1=[CH:15][C:16](Br)=[CH:17][CH:18]=3)=[CH:2]2.[CH3:40][C:41]1[CH:46]=[CH:45][CH:44]=[C:43]([NH:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH:42]=1>C1(C)C=CC=CC=1>[C:1]12[CH2:8][CH2:7][C:6]=1[CH:5]=[CH:4][C:3]([CH2:9][CH2:10][CH2:11][CH2:12][C:13]1([CH2:28][CH2:29][CH2:30][CH2:31][C:32]3[CH:33]=[C:34]4[C:37](=[CH:38][CH:39]=3)[CH2:36][CH2:35]4)[C:25]3[CH:24]=[C:23]([N:47]([C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)[C:43]4[CH:42]=[C:41]([CH3:40])[CH:46]=[CH:45][CH:44]=4)[CH:22]=[CH:21][C:20]=3[C:19]3[C:14]1=[CH:15][C:16]([N:47]([C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1)[C:43]1[CH:42]=[C:41]([CH3:40])[CH:46]=[CH:45][CH:44]=1)=[CH:17][CH:18]=3)=[CH:2]2

Participants

4

Reactant 2

HCID 14569N-(3-Methylphenyl)anilineHCID 580284989-(4-(bicyclo[4.2.0]octa-1(6),2,4-trien-3-yl)butyl)-9-(4-(bicyclo[4.2.0]octa-1,3,5-trien-3-yl)butyl)-2,7-dibromo-9H-fluorene

Product 1

HCID 58028469HCID 58028469, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To an oven-dried three-neck round-bottom flask under nitrogen, were added 600 mL anhydrous toluene, 14.3 g 9-(4-(bicyclo[4.2.0]octa-1(6),2,4-trien-3-yl)butyl)-9-(4-(bicyclo[4.2.0]octa-1,3,5-trien-3-yl)butyl)-2,7-dibromo-9H-fluorene, and 9.2 mL 3-methyldiphenylamine. After the reaction mixture was degassed with strong nitrogen flow for 30 minutes, 6.44 g sodium tert-butoxide, 0.82 g tris(dibenzylideneacetone)dipalladium(0) (Pd2dba3), and 0.54 g tri-tert-butyl phosphine in 15 mL toluene were added. The reaction mixture was heated to reflux. After three hours, the heating was turn off, and the reaction was allowed to cool down to room temperature. The reaction mixture was filter through a Celite/silica gel plug. The product (13.1 g) was purified by flash chromatography using hexane, 1% then 5% ethyl acetate in hexane solution. The structure was confirmed by NMR.

Workup

  1. customAfter the reaction mixture was degassed with strong nitrogen flow for 30 minutes
  2. addition6.44 g sodium tert-butoxide, 0.82 g tris(dibenzylideneacetone)dipalladium(0) (Pd2dba3), and 0.54 g tri-tert-butyl phosphine in 15 mL toluene were added
  3. temperatureThe reaction mixture was heated to reflux
  4. filtrationThe reaction mixture was filter through a Celite/silica gel plug
  5. customThe product (13.1 g) was purified by flash chromatography

Sources & evidence

ORD record
ord-b46fee9b76c24f3ca9805eb4a18a6229
Source dataset
uspto-grants-2013_09
Patent number
US08535974B2

Reaction notes

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