Triphenylphosphine → 3-[2-(2-Oxo-pyrrolidin-1-yl)-ethoxy]-indeno[1,2-b]pyridin-5-one

HRID 541152Notes

Reaction equation

HRID 541152 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:14](=[O:15])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:5]2=[N:6][CH:7]=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:52][CH2:53][N:54]1[CH2:58][CH2:57][CH2:56][C:55]1=[O:59]>O1CCCC1>[O:59]=[C:55]1[CH2:56][CH2:57][CH2:58][N:54]1[CH2:53][CH2:52][O:1][C:2]1[CH:3]=[C:4]2[C:14](=[O:15])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 769801-(2-Hydroxyethyl)-2-pyrrolidinoneHCID 97268Di-tert-butyl azodicarboxylateHCID 594925083-Hydroxy-indeno[1,2-b]pyridin-5-one

Product 1

HCID 594925093-[2-(2-Oxo-pyrrolidin-1-yl)-ethoxy]-indeno[1,2-b]pyridin-5-oneYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Hydroxy-indeno[1,2-b]pyridin-5-one (0.0500 g), di-t-butyl azodicarboxylate (0.087 g) and triphenylphosphine (0.10 g) were mixed with tetrahydrofuran (1.0 ml), 1-(2-hydroxy-ethyl)-2-pyrrolidone (0.043 ml) was added thereto, and the mixture was stirred at room temperature for 1 day. The mixture was purified by preparative thin layer chromatography (silica gel, eluent:ethyl acetate/methanol=10/1) to give the title compound (0.0386 g, 49%).

Workup

  1. additionwas added
  2. customThe mixture was purified by preparative thin layer chromatography (silica gel, eluent:ethyl acetate/methanol=10/1)

Sources & evidence

ORD record
ord-f5748057c0644ff3a18a6d81e22af083
Source dataset
uspto-grants-2014_10
Patent number
US08871934B2

Reaction notes

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