Water → HCID 58392203, compound

HRID 561583Notes

Reaction equation

HRID 561583 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)O)=[CH:4][CH:3]=1.[Cl-].[In+3].[Cl-].[Cl-].ClC1C=C(Cl)C=CC=1C([C:33]1[C:41]2[C:36](=[C:37]([CH2:43][S:44][CH3:45])[CH:38]=[C:39](F)[CH:40]=2)[NH:35][CH:34]=1)CCO.O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[C:33]2[C:41]3[C:36](=[C:37]([CH2:43][S:44][CH3:45])[CH:38]=[CH:39][CH:40]=3)[NH:35][CH:34]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 159675indium(III)chlorideHCID 12634874(4-Chlorophenyl)(4-fluorophenyl)methanolHCID 583923053-(2,4-Dichlorophenyl)-3-{5-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propan-1-ol

Product 1

HCID 58392203HCID 58392203, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

2.94 g (12.41 mmol) of the compound from Example 81A and 2.50 g (11.28 mmol) of indium(III) chloride were added to 2.00 g (11.28 mmol) of the compound from Example 8 in 100 ml of toluene. The reaction mixture was stirred at 80° C. for 3 h. After cooling to RT, the reaction solution was mixed with water and ethyl acetate and the solid was filtered off. 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 0.83 g (19% of theory) of the title compound.

Workup

  1. temperatureAfter cooling to RT
  2. filtrationthe solid was filtered off
  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-f82843f8ab13408c9b2b316e0f3d0001
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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