Potassium Carbonate → HCID 178506374, compound

HRID 2042745Notes

Reaction equation

HRID 2042745 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][C:10]([F:13])([F:12])[F:11].[O:14]1[C:18]2([CH2:23][CH2:22][CH:21]([C:24]3[N:29]=[CH:28][C:27]([C:30]4[CH:34]=[C:33]([OH:35])[NH:32][N:31]=4)=[CH:26][CH:25]=3)[CH2:20][CH2:19]2)[O:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[O:14]1[C:18]2([CH2:19][CH2:20][CH:21]([C:24]3[CH:25]=[CH:26][C:27]([C:30]4[CH:34]=[C:33]([O:35][CH2:2][C:3]5[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=5[O:9][C:10]([F:13])([F:12])[F:11])[NH:32][N:31]=4)=[CH:28][N:29]=3)[CH2:22][CH2:23]2)[O:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27772542-(Trifluoromethoxy)benzyl bromideHCID 178515509HCID 178515509, compound

Product 1

HCID 178506374HCID 178506374, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

1-(bromomethyl)-2-(trifluoromethoxy)benzene (0.4 g, 1.57 mmol) was added dropwise to a stirred solution of Example 93D (0.43 g, 1.42 mmol) and potassium carbonate (0.16 g, 1.13 mmol) in refluxing dry acetone (7 mL). The resulting solution was heated (50° C.) for another 1 hour before the solvent was evaporated and the residue was partitioned using brine and ethyl acetate. The organic phase was dried (magnesium sulfate), filtered, and concentrated. The residue was purified by silica gel chromatography using 0 to 100% ethyl acetate in hexanes to provide the title compound as a yellow oil.

Workup

  1. customwas evaporated
  2. customthe residue was partitioned
  3. dry with materialThe organic phase was dried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-379b1fabbe4246409e4db8a5215ddbcd
Source dataset
uspto-grants-2013_11
Patent number
US08586594B2

Reaction notes

Loading…