Cesium carbonate → HCID 25115871, compound

HRID 408658Notes

Reaction equation

HRID 408658 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:16][CH2:15][CH:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:23])[CH:8]=2)[N:3]=1.Br[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([CH3:35])(=[O:34])=[O:33])=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[CH3:35][S:32]([C:29]1[CH:30]=[CH:31][C:26]([CH2:25][O:23][C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[N:3]=[C:2]([CH3:1])[CH:11]=[C:10]3[N:12]2[CH2:16][CH2:15][CH:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13]2)=[CH:27][CH:28]=1)(=[O:33])=[O:34]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27335814-(Methylsulfonyl)benzyl BromideHCID 68725752HCID 68725752, compound

Product 1

HCID 25115871HCID 25115871, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-Methyl-4-(3-phenylpyrrolidin-1-yl)quinolin-6-ol (0.05 g; see Example 42 below), 1-bromomethyl-4-methanesulfonylbenzene (0.08 g), caesium carbonate (0.1 g) in DMF (2 mL) was heated in a microwave at 120° C. for 15 minutes. The reaction mixture was diluted with water and extracted with dichloromethane, washed with water, dried (MgSO4), filtered and evaporated to give an oil. The residue was purified by chromatography on silica, eluting with a mixture of dichloromethane, and methanol. Evaporation of the desired fractions gave the title compound as a pale yellow solid.

Workup

  1. extractionextracted with dichloromethane
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customto give an oil
  7. customThe residue was purified by chromatography on silica
  8. washeluting with a mixture of dichloromethane, and methanol
  9. customEvaporation of the desired fractions

Sources & evidence

ORD record
ord-15a56ae018d0454485f36fbabfeeab46
Source dataset
uspto-grants-2014_06
Patent number
US08759348B2

Reaction notes

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