Toluene → 6-((2,5-diphenyl-1H-pyrrol-1-yl)methyl)pyridin-2-amine

HRID 15016Notes

Reaction equation

HRID 15016 reaction equation
[NH2:1][CH2:2][C:3]1[N:8]=[C:7]([NH2:9])[CH:6]=[CH:5][CH:4]=1.C1(C)C=CC=CC=1.CC1C=CC(S(O)(=O)=O)=CC=1.[C:28]1([C:34](=O)[CH2:35][CH2:36][C:37]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CCO>[C:28]1([C:34]2[N:1]([CH2:2][C:3]3[N:8]=[C:7]([NH2:9])[CH:6]=[CH:5][CH:4]=3)[C:37]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)=[CH:36][CH:35]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 1363221,4-Diphenyl-1,4-butanedioneHCID 179589636-Amino-2-pyridinemethanamine

Product 1

HCID 115733956-((2,5-diphenyl-1H-pyrrol-1-yl)methyl)pyridin-2-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-(Aminomethyl)pyridin-2-amine (0.050 g, 0.4 mmol) was dissolved in EtOH (2 mL) and Toluene (10 mL) was added. To this mixture was added pTSA (5 mg) and 1,4-diphenyl-1,4-butanedione (0.124 g, 0.4 mmol). The solution was heated to reflux overnight. The solvent was removed and the residue was purified by flash chromatography (20:1 CHCl3: MeOH) to yield 6-[(2,5-diphenyl-1H-pyrrol-1-yl)methyl]pyridin-2-amine as a white solid. mp 143-144° C.; 1H NMR (500 MHz, DMSO-d6) δ: 5.06 (s, 2H), 5.50 (d, 1H, J=7.3 Hz), 5.82 (s, 2H), 6.16 (d, 1H, J=8.1 Hz), 6.34 (s, 2H), 7.18 (t, 1H, J=7.47 Hz), 7.28 (t, 2H, J=8.5 Hz), 7.36 (m, 4H), 7.40 (m, 4H); MS (ES) m/z 326.3.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux overnight
  3. customThe solvent was removed
  4. customthe residue was purified by flash chromatography (20:1 CHCl3: MeOH)

Sources & evidence

ORD record
ord-b75dbfffe23748eba186fe2977bc1c9f
Source dataset
uspto-grants-2010_06
Patent number
US07732457B2

Reaction notes

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