Sodium Carbonate → (R)-4-((R)-1-(6,7'-biquinolin-5'-yloxy)ethyl)pyrrolidin-2-one

HRID 1496869Notes

Reaction equation

HRID 1496869 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[C:4]([O:12][C@@H:13]([C@H:15]2[CH2:19][NH:18][C:17](=[O:20])[CH2:16]2)[CH3:14])[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCOCC1>[N:9]1[C:10]2[C:5](=[CH:4][C:3]([C:2]3[CH:11]=[C:10]4[C:5]([CH:6]=[CH:7][CH:8]=[N:9]4)=[C:4]([O:12][C@@H:13]([C@H:15]4[CH2:19][NH:18][C:17](=[O:20])[CH2:16]4)[CH3:14])[CH:3]=3)=[CH:2][CH:11]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 71238288(R)-4-((R)-1-(7-bromoquinolin-5-yloxy)ethyl)pyrrolidin-2-one

Product 1

HCID 71238173(R)-4-((R)-1-(6,7'-biquinolin-5'-yloxy)ethyl)pyrrolidin-2-oneYield 131.1%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

40 mg Example 27, 31 mg quinoline-6-boronic acidboronic acid, 14 mg tetrakis-(triphenylphosphin)-palladium(0), 120 μL 2N aqueous sodium carbonate and 0.5 mL dioxan were heated in the microwave (MW) for 15 min at 140° C. The mixture was purified with HPLC (XbridgeC18, MeOH/water, TFA) and the desired fractions lyophilized to yield 30 mg (75%) of Example 29 as yellow solid.

Workup

  1. customwere heated in the microwave (MW) for 15 min at 140° C
  2. customThe mixture was purified with HPLC (XbridgeC18, MeOH/water, TFA)

Sources & evidence

ORD record
ord-05fe280d473c44b0acd1bd4dd9af38e3
Source dataset
uspto-grants-2015_12
Patent number
US09199937B2

Reaction notes

Loading…