Potassium Iodide → HCID 46940553, compound

HRID 1095866Notes

Reaction equation

HRID 1095866 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:23])[CH:5]=[CH:6][C:7]=1[CH:8]([CH3:22])[C:9]([OH:21])([C:14]1[CH:19]=[N:18][C:17]([CH3:20])=[CH:16][N:15]=1)[C:10]([F:13])([F:12])[F:11].Br[CH2:25][C:26]1[CH:36]=[CH:35][C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:28][CH:27]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:33]([O:32][C:30](=[O:31])[C:29]1[CH:35]=[CH:36][C:26]([CH2:25][O:23][C:4]2[CH:5]=[CH:6][C:7]([CH:8]([CH3:22])[C:9]([OH:21])([C:14]3[CH:19]=[N:18][C:17]([CH3:20])=[CH:16][N:15]=3)[C:10]([F:13])([F:11])[F:12])=[C:2]([Cl:1])[CH:3]=2)=[CH:27][CH:28]=1)[CH3:34]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 954261Ethyl 4-(bromomethyl)benzoateHCID 574212313-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(5-methyl-pyrazin-2-yl)-propyl]-phenol

Product 1

HCID 46940553HCID 46940553, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(5-methyl-pyrazin-2-yl)-propyl]-phenol (120 mg, 0.35 mmol) in acetone (3 ml) were added ethyl 4-(bromomethyl)benzoate (197 mg, 0.78 mmol), potassium iodide (9 mg, 0.05 mmol) and potassium carbonate (108 mg, 0.78 mmol). The mixture was stirred for 17 h at 60° C. The reaction mixture was concentrated. Water and EtOAc were added and the mixture was extracted with EtOAc. The combined organic phases were washed with brine, dried over MgSO4, filtered and concentrated. The product was purified by flash chromatography (20 g silica gel, heptane/EtOAc 9:1) to give title compound as colorless viscous oil (133 mg). MS (m/e, ISP neg. ion)=507.1 [M−H+].

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionWater and EtOAc were added
  3. extractionthe mixture was extracted with EtOAc
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was purified by flash chromatography (20 g silica gel, heptane/EtOAc 9:1)

Sources & evidence

ORD record
ord-fa3259b8983a4522a20a41a5b26cbc68
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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