HCID 68452514, compound → HCID 68452515, compound

HRID 2355118Notes

Reaction equation

HRID 2355118 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]([NH:19][CH2:20][C:21]([C:23]2[CH:32]=[CH:31][C:30]3[C:25](=[CH:26][CH:27]=[C:28]([O:33][CH3:34])[CH:29]=3)[CH:24]=2)=[O:22])=O)=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C2C(=CC=CC=2)C(C2OC(C3C=CC4C(=CC=C(OC)C=4)C=3)=CN=2)=C1)C1C=CC=CC=1>O=P(Cl)(Cl)Cl>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]2[O:22][C:21]([C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][CH:27]=[C:28]([O:33][CH3:34])[CH:29]=4)[CH:24]=3)=[CH:20][N:19]=2)=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 68452514HCID 68452514, compound

Product 1

HCID 68452515HCID 68452515, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

1-Benzyl-3-[5-(6-methoxy-2-naphthyl)-1,3-oxazol-2-yl]-1H-indole 1-Benzyl-N-[2-(6-methoxy-2-naphthyl)-2-oxoethyl]-1H-indole-3-carboxamide (4.31 g, 9.61 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 and then allowed to air dry overnight. The solid was taken up in 90% CH2Cl2/CH3OH, extracted three times with 5% NaHCO3, dried (MgSO4), filtered and the solvent was removed under reduced pressure to give 1-benzyl-3-[5-(6-methoxy-2-naphthyl)-1,3-oxazol-2-yl]-1H-indole (3.09 g, 75%) as an off-white solid, mp 198-199° C. Elemental Analysis for C29H22N2O2 Calc'd: C, 80.91; H, 5.15; N, 6.51. Found: C, 78.79; H, 5.25; N, 6.16.

Workup

  1. temperaturewas refluxed for 4 h
  2. customprecipitated
  3. filtrationThe solid was collected by filtration
  4. customto air dry overnight
  5. extractionextracted three times with 5% NaHCO3
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ae6972de476e49d689a684362d0d73c1
Source dataset
uspto-grants-2010_07
Patent number
US07754747B2

Reaction notes

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