4'-Chloropropiophenone → HCID 58392487, compound

HRID 561608Notes

Reaction equation

HRID 561608 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](O)([CH2:12][CH3:13])[CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.ClC1C=CC(C(=O)CC)=CC=1.[Cl-].[In+3].[Cl-].[Cl-].[CH3:30][S:31][CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[C:37]2[C:41]=1[NH:40][CH:39]=[CH:38]2>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:38]2[C:37]3[C:41](=[C:33]([CH2:32][S:31][CH3:30])[CH:34]=[CH:35][CH:36]=3)[NH:40][CH:39]=2)([CH2:12][CH3:13])[CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 226974'-ChloropropiophenoneHCID 159675indium(III)chlorideHCID 583921877-[(Methylsulfanyl)methyl]-1H-indoleHCID 670008003-(4-Chlorophenyl)pentane-1,3-diol

Product 1

HCID 58392487HCID 58392487, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
80 °C

Procedure

3.04 g (14.10 mmol) of 3-(4-chlorophenyl)pentane-1,3-diol (preparation in analogy to the synthesis of Example 88A and 89A starting from 1-(4-chloropenyl)propan-1-one and ethyl acetate) and 3.12 g (14.10 mmol) of indium(III) chloride were added to 2.50 g (14.10 mmol) of the compound from Example 8A in 60 ml of toluene. The reaction mixture was stirred at 80° C. for 5 h. After cooling to RT, the reaction solution was mixed with water and ethyl acetate, and the solid was filtered off through kieselguhr. The phases of the filtrate were separated, and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated. Purification of the crude product by preparative HPLC (mobile phase: acetonitrile/water gradient) resulted in 2.13 g (40% of theory) of the title compound.

Workup

  1. temperatureAfter cooling to RT
  2. filtrationthe solid was filtered off through kieselguhr
  3. customThe phases of the filtrate were separated
  4. extractionthe aqueous phase was extracted with ethyl acetate
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification of the crude product by preparative HPLC (mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-0500203b14c6440fa005ddf0e0cb81cc
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

Loading…