Diphenyl Ether → 4-(1H-Indol-1-yl)-N,6-dimethylpyridin-2-amine

HRID 2255919Notes

Reaction equation

HRID 2255919 reaction equation
[N:1]1([C:10]2[CH:15]=[C:14]([CH3:16])[N:13]=[C:12]([NH:17][CH3:18])[CH:11]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C1(OC2C=CC=CC=2)C=CC=CC=1>[Pd].C(OCC)C>[N:1]1([C:10]2[CH:15]=[C:14]([CH3:16])[N:13]=[C:12]([NH:17][CH3:18])[CH:11]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 2

HCID 7583Diphenyl EtherHCID 19029083HCID 19029083, compound

Product 1

HCID 190290604-(1H-Indol-1-yl)-N,6-dimethylpyridin-2-amineYield 94.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4-(1-indolinyl)-6-methyl-2-(methylamino)pyridine (0.45 g, 1.88 mM), 30% w/w palladium on charcoal (0.045 g) and diphenyl ether (10 ml) was heated under reflux for 45 minutes. The mixture was cooled. Diethyl ether (50 ml) was added and the catalyst removed by filtration through diatomaceous earth. The filter cake was washed with diethyl ether (50 ml). The filtrate and washings were concentrated under reduced pressure. The yellow solid obtained was further purified by flash chromatography (Merck 9385 silica, 100 g) eluting with diethyl ether to give 4-(1-indolyl)-6-methyl-2-methylaminopyridine as a solid (0.42 g, 90% yield), m.p. 156°-158° C.; NMR (CDCl3): 2.45(3H,s,CH3), 2.9-3.0(3H,d,NHCH3), 4.75-4.85(1H,br, NH), 6.3(1H,s, pyridine-3H), 6.6-6.7(2H, complex, pyridine-5H and indole-3H), 7.15-7.4(3H, complex, indole-2H and aromatic), 7.65-7.75(2H, complex, aromatic).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 45 minutes
  3. temperatureThe mixture was cooled
  4. customthe catalyst removed by filtration through diatomaceous earth
  5. washThe filter cake was washed with diethyl ether (50 ml)
  6. concentrationThe filtrate and washings were concentrated under reduced pressure
  7. customThe yellow solid obtained
  8. customwas further purified by flash chromatography (Merck 9385 silica, 100 g)
  9. washeluting with diethyl ether

Sources & evidence

ORD record
ord-5cd247c2f6c642f780d6d4a474f9c505
Source dataset
uspto-grants-1997_08
Patent number
US05654298

Reaction notes

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