Hydrogen Bromide → HCID 21865552, compound

HRID 896652Notes

Reaction equation

HRID 896652 reaction equation
[CH3:1][S:2]([C:5]([C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([C:18]3[CH:19]=[C:20]([CH2:24]O)[CH:21]=[CH:22][CH:23]=3)[CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)([CH3:7])[CH3:6])(=[O:4])=[O:3].[BrH:26].C1COCC1.[OH-].[Na+]>CC(O)=O>[Br:26][CH2:24][C:20]1[CH:19]=[C:18]([C:16]2[CH:17]=[C:8]([C:5]([S:2]([CH3:1])(=[O:4])=[O:3])([CH3:7])[CH3:6])[CH:9]=[C:10]3[C:15]=2[N:14]=[CH:13][CH:12]=[CH:11]3)[CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21865637HCID 21865637, compound

Product 1

HCID 21865552HCID 21865552, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of the {3-[6-(1-Methanesulfonyl-1-methyl-ethyl)-quinolin-8-yl]-phenyl}-methanol compound from Step 3 above (30 g, 85 mmol) in AcOH (140 mL) and HBr (48 mL, 48% aq) was stirred for 18 h at 80° C. The resulting mixture was cooled to 0° C. and poured into 2L of cold NaOH (0.3N). The pH of the resulting solution was adjusted to 5 and filtered. The resulting solid was dissolved in EtOAc, washed with saturated NaHCO3 solution, brine, dried (MgSO4), filtered and concentrated. Stirring the solid in ether/EtOAc, followed by filtration gave desired 8-(3-Bromomethyl-phenyl)-6-(1-methanesulfonyl-1-methyl-ethyl)-quinoline as a pale brown solid.

Workup

  1. filtrationfiltered
  2. dissolutionThe resulting solid was dissolved in EtOAc
  3. washwashed with saturated NaHCO3 solution, brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. filtrationfollowed by filtration

Sources & evidence

ORD record
ord-f9875a1bcbb24a44a8abab5b9d1fde20
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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