Dimethylformamide → HCID 10128861, compound

HRID 857303Notes

Reaction equation

HRID 857303 reaction equation
N1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.O[C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][C:13]=1[C:22](=[O:24])[CH3:23].[C:25]([O-:28])([O-])=O.[Cs+].[Cs+].[CH3:31][N:32]([CH:34]=O)C>[NH4+].[Cl-]>[CH3:21][S:18]([C:15]1[CH:16]=[CH:17][C:12]([O:28][CH2:25][C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([C:4]3[CH:3]=[C:2]([C:15]([S:18]([CH3:21])(=[O:20])=[O:19])([CH3:16])[CH3:14])[CH:17]=[C:12]4[C:31]=3[N:32]=[CH:34][CH:22]=[CH:13]4)[CH:6]=2)=[C:13]([C:22](=[O:24])[CH3:23])[CH:14]=1)(=[O:20])=[O:19]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7047QuinolineHCID 10796Cesium carbonateHCID 12791432HCID 12791432, compound

Product 1

HCID 10128861HCID 10128861, compound

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Procedure

To solution of Quinoline 12 (1.0 eq) and 1-(2-hydroxy-5-methanesulfonyl-phenyl)-ethanone (1.08 eq) (from the procedure described in Synthesis, 1982, 11, 940) in DMF (0.05M) was added Cs2CO3 (1.08 eq). The mixture was stirred for 12 h then poured in saturated aqueous NH4Cl and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. Flash chromatography (CH2Cl2:EtOAc; 50 to 100%) afforded the title compound as a white solid.

Workup

  1. extractionextracted with EtOAc (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-fa6ef281ec554a6da4c63ea6ed80e742
Source dataset
uspto-grants-2006_12
Patent number
US07144896B2

Reaction notes

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