Quinoline → HCID 10288039, compound

HRID 857280Notes

Reaction equation

HRID 857280 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:11]([O-:14])([O-])=O.[Cs+].[Cs+].Cl[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=1>CC(C)=O.O>[CH:8]([C:7]1[CH:6]=[C:5]2[C:10](=[C:9]([C:3]3[CH:4]=[CH:5][CH:6]=[C:11]([O:14][CH2:18][C:19]4[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=4)[CH:2]=3)[CH:8]=1)[N:1]=[CH:2][CH:3]=[CH:4]2)([CH3:9])[CH3:7]

Participants

6

Reactant 3

HCID 7047QuinolineHCID 10796Cesium carbonateHCID 1235301-(Chloromethyl)-4-methanesulfonylbenzene

Product 1

HCID 10288039HCID 10288039, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of Quinoline 2 (1.0 eq) in acetone (0.2M) was added Cs2CO3 (1.5 eq) and 1-chloromethyl-4-methanesulfonyl-benzene (1.5 eq). The resulting mixture was stirred 2 days at room temperature, poured in water and extracted with Et2O (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. Flash chromatography (Hex:EtOAc; 9:1 to 1:9 in 15 min) afforded the title compound as a white solid.

Workup

  1. extractionextracted with Et2O (2×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0bb94a6f39d04bb5b8d6467f4b65311b
Source dataset
uspto-grants-2006_12
Patent number
US07144896B2

Reaction notes

Loading…