indium(III)chloride → HCID 58392362, compound

HRID 561723Notes

Reaction equation

HRID 561723 reaction equation
[Cl-].[In+3].[Cl-].[Cl-].C(O[CH:9]([CH:20]1[CH2:22][C:21]1([F:24])[F:23])[C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1)(=O)C.[CH3:25][S:26]([CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[C:34]2[C:38]=1[NH:37][CH:36]=[CH:35]2)(=[O:28])=[O:27].C(=O)(O)[O-].[Na+]>ClCCCl.C(OCC)(=O)C>[F:24][C:21]1([F:23])[CH2:22][CH:20]1[CH:9]([C:10]1[CH:11]=[CH:12][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:14][CH:15]=1)[C:35]1[C:34]2[C:38](=[C:30]([CH2:29][S:26]([CH3:25])(=[O:28])=[O:27])[CH:31]=[CH:32][CH:33]=2)[NH:37][CH:36]=1

Participants

7

Reactant 4

HCID 159675indium(III)chloride2×HCID 516892Sodium BicarbonateHCID 583922947-[(Methylsulfonyl)methyl]-1H-indoleHCID 58392447HCID 58392447, compound

Product 1

HCID 58392362HCID 58392362, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.05 g (9.27 mmol) of indium(III) chloride were added to 2.50 g (8.50 mmol) of the compound from Example 192A and 1.62 g (7.72 mmol) of the compound from Example 86A in 31 ml of 1,2-dichloroethane under argon and reflux, and the mixture was heated under reflux for 2.5 h. A further 2.00 g (9.04 mmol) of indium(III) chloride were added, and the mixture was heated under reflux for a further 2 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 1/1) and by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient) to result in 13.0 mg (0.3% of theory) of the title compound as mixture of diastereomers.

Workup

  1. temperaturereflux
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 2.5 h
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for a further 2 h
  6. customdrying of the organic phase and concentration
  7. customThe residue was purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 1/1) and by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-9ddc1b0210fa4e888309648d53129e19
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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