indium(III)chloride → HCID 44595095, compound

HRID 561724Notes

Reaction equation

HRID 561724 reaction equation
[Cl-].[In+3].[Cl-].[Cl-].C(O[CH:9]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[Cl:22])[CH:10]1[CH2:12][C:11]1([F:14])[F:13])(=O)C.[CH3:23][S:24]([CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[C:32]2[C:36]=1[NH:35][CH:34]=[CH:33]2)(=[O:26])=[O:25].C(=O)(O)[O-].[Na+]>ClCCCl.C(OCC)(=O)C>[Cl:22][C:16]1[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=1[CH:9]([CH:10]1[CH2:12][C:11]1([F:13])[F:14])[C:33]1[C:32]2[C:36](=[C:28]([CH2:27][S:24]([CH3:23])(=[O:26])=[O:25])[CH:29]=[CH:30][CH:31]=2)[NH:35][CH:34]=1

Participants

7

Reactant 4

HCID 159675indium(III)chlorideHCID 516892Sodium BicarbonateHCID 58392161HCID 58392161, compoundHCID 583922947-[(Methylsulfonyl)methyl]-1H-indole

Product 1

HCID 44595095HCID 44595095, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.64 g (7.39 mmol) of indium(III) chloride were added to 2.00 g (6.78 mmol) of the compound from Example 193A and 1.29 g (6.16 mmol) of the compound from Example 86A in 20 ml of 1,2-dichloroethane under argon and reflux, and the mixture was heated under reflux for 1.5 h. This was followed by addition of ethyl acetate and saturated aqueous sodium bicarbonate solution, separation of the phases, drying of the organic phase and concentration. The residue was purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 2/1 and 1/1) and by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient) to result in 28.0 mg (1% of theory) of diastereomer 1 and 28.0 mg (1% of theory) of diastereomer 2 of the title compound.

Workup

  1. temperaturereflux
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 1.5 h
  4. customdrying of the organic phase and concentration
  5. customThe residue was purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 2/1 and 1/1) and by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-1ec9afc3a34a415aa7fc3e5365da8b13
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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