5-(2-(4-(4-Fluoro-2-methyl-1H-indol-5-yloxy)-6-methoxyquinolin-7-yloxy)ethyl)-5-azaspiro[2.4]-heptan-7-one → 4-(4-Fluoro-2-methyl-1H-indol-5-yloxy)-6-methoxy-7-(2-(7-methylene-5-azaspiro[2.4]heptan-5-yl)ethoxy)quinoline

HRID 1510107Notes

Reaction equation

HRID 1510107 reaction equation
[F:1][C:2]1[C:10]([O:11][C:12]2[C:21]3[C:16](=[CH:17][C:18]([O:24][CH2:25][CH2:26][N:27]4[CH2:33][C:32](=O)[C:29]5([CH2:31][CH2:30]5)[CH2:28]4)=[C:19]([O:22][CH3:23])[CH:20]=3)[N:15]=[CH:14][CH:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:35])[NH:6]2.Br[Zn][CH2:38][Zn]C[Zn]Br.C1OCCC1>O1CCCC1>[F:1][C:2]1[C:10]([O:11][C:12]2[C:21]3[C:16](=[CH:17][C:18]([O:24][CH2:25][CH2:26][N:27]4[CH2:33][C:32](=[CH2:38])[C:29]5([CH2:30][CH2:31]5)[CH2:28]4)=[C:19]([O:22][CH3:23])[CH:20]=3)[N:15]=[CH:14][CH:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:35])[NH:6]2

Participants

4

Reactant 2

HCID 461764815-(2-(4-(4-Fluoro-2-methyl-1H-indol-5-yloxy)-6-methoxyquinolin-7-yloxy)ethyl)-5-azaspiro[2.4]-heptan-7-oneHCID 178420636HCID 178420636, compound

Product 1

HCID 461765604-(4-Fluoro-2-methyl-1H-indol-5-yloxy)-6-methoxy-7-(2-(7-methylene-5-azaspiro[2.4]heptan-5-yl)ethoxy)quinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The above product from Example 2 (50 mg) was dissolved into anhydrous tetrahydrofuran (5 ml) and Nysted reagent (1.5 eq, 20% solution) was added to the reaction. The reaction was stirred at RT for two days and quenched with NH4Cl solution and extracted with EtOAc followed by washing with water, then brine and dried over Na2SO4 and purified with silica gel column to give the titled compound. Mass: (M+1), 474

Workup

  1. additionwas added to the reaction
  2. customquenched with NH4Cl solution
  3. extractionextracted with EtOAc
  4. washby washing with water
  5. dry with materialbrine and dried over Na2SO4
  6. custompurified with silica gel column

Sources & evidence

ORD record
ord-956bec37a7584f1aa21356893e5544e7
Source dataset
uspto-grants-2012_07
Patent number
US08211911B2

Reaction notes

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