Hydrochloric Acid → HCID 66668689, compound

HRID 1617552Notes

Reaction equation

HRID 1617552 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([O:18]C)[CH:13]=2)=[O:11])=[CH:4][CH:3]=1.Cl.O.CCOC(C)=O>O1CCOCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][NH:15][C:14](=[O:18])[CH:13]=2)=[O:11])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 67015529HCID 67015529, compound

Product 1

HCID 66668689HCID 66668689, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-(4-bromo-phenyl)-1-(2-methoxy-pyridin-4-yl)-3-o-tolyl-propan-1-one (example 109, step 1; 190 mg) in dioxane (9 mL) was added concentrated hydrochloric acid (1 mL) and the mixture was heated to 100° C. for 2 h. The solution was cooled to rt and added to a mixture of water and EtOAc. The inorganic phase was extracted with EtOAc and the combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to yield the crude title compound as a white foam, MS (ESI+): m/z=396.1 ([M+H]+, 1Br).

Workup

  1. temperatureThe solution was cooled to rt
  2. extractionThe inorganic phase was extracted with EtOAc
  3. washthe combined organic phases were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-61cc80ec492249b4a8dacb6870707937
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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