1-methyl-N-[2-(6-methoxy-2-naphthyl)-2-oxoethyl]-1H-indole-3-carboxamide → 3-[5-(6-methoxy-2-naphthyl)-1,3-oxazol-2-yl]-1-methyl-1H-indole

HRID 2355125Notes

Reaction equation

HRID 2355125 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([NH:13][CH2:14][C:15]([C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([O:27][CH3:28])[CH:23]=3)[CH:18]=2)=O)=[O:12])=[CH:3]1>O=P(Cl)(Cl)Cl>[CH3:28][O:27][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][CH:21]=1)[CH:18]=[C:17]([C:15]1[O:12][C:11]([C:4]3[C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:2]([CH3:1])[CH:3]=3)=[N:13][CH:14]=1)[CH:26]=[CH:25]2

Participants

3

Reactant 1

HCID 684532481-methyl-N-[2-(6-methoxy-2-naphthyl)-2-oxoethyl]-1H-indole-3-carboxamide

Product 1

HCID 684536803-[5-(6-methoxy-2-naphthyl)-1,3-oxazol-2-yl]-1-methyl-1H-indoleYield 250.6%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

1-Methyl-N-[2-(6-methoxy-2-naphthyl)-2-oxoethyl]-1H-indole-3-carboxamide (3.68 g 2.68 mmol), prepared in the previous step, in 200 mL of POCl3 was refluxed for 4 h. As the reaction cooled to room temperature a solid precipitated. The solid was collected by filtration, rinsed with 10 mL of methylene chloride and dried under reduced pressure. The solid was then taken up in 80% CH2Cl2/CH3OH, extracted three times with 5% NaHCO3, dried (MgSO4), filtered and the solvent was removed under reduced pressure to give 3-[5-(6-methoxy-2-naphthyl)-1,3-oxazol-2-yl]-1-methyl-1H-indole (2.38 g, 68%) as a light yellow solid, mp 187-189° C. Elemental Analysis for C23H18N2O2 Calc'd: C, 77.95; H, 5.12; N, 7.90. Found: C, 77.16; H, 5.10; N, 7.77.

Workup

  1. temperaturewas refluxed for 4 h
  2. customprecipitated
  3. filtrationThe solid was collected by filtration
  4. washrinsed with 10 mL of methylene chloride
  5. customdried under reduced pressure
  6. extractionextracted three times with 5% NaHCO3
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4155b96b20344cf9a7b8f6b4c2963f1c
Source dataset
uspto-grants-2010_07
Patent number
US07754747B2

Reaction notes

Loading…