Hydrogen Bromide → HCID 69375565, compound

HRID 860987Notes

Reaction equation

HRID 860987 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]([C:24]4[CH:29]=[CH:28][C:27]([CH2:30]O)=[CH:26][CH:25]=4)[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:32].O.[OH-].[Na+]>CC(O)=O>[Br:32][CH2:30][C:27]1[CH:28]=[CH:29][C:24]([C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([C:16]3[CH:17]=[C:8]([C:5]([S:2]([CH3:1])(=[O:4])=[O:3])([CH3:7])[CH3:6])[CH:9]=[C:10]4[C:15]=3[N:14]=[CH:13][CH:12]=[CH:11]4)[CH:19]=2)=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 962WaterHCID 14798Sodium HydroxideHCID 10320554HCID 10320554, compound

Product 1

HCID 69375565HCID 69375565, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of {3′-[6-(1-methanesulfonyl-1-methyl-ethyl)-quinolin-8-yl]-biphenyl-4-yl}-methanol from Step 1 (1.0 eq.) in AcOH (0.3M) was added HBr (48%; 9.5 eq.). The mixture was stirred at 80° C. for 12 h, cooled to rt, poured in cold water containing 10 eq. of NaOH and extracted with EtOAc. The organic extract was washed with saturated aqueous NaHCO3 (3×), brine, dried over Na2SO4, filtered and concentrated to afford the title compound as a yellow solid.

Workup

  1. temperaturecooled to rt
  2. extractionextracted with EtOAc
  3. extractionThe organic extract
  4. washwas washed with saturated aqueous NaHCO3 (3×), brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7a3717661817438c9d851186e8cfc83c
Source dataset
uspto-grants-2006_12
Patent number
US07153968B2

Reaction notes

Loading…