Trifluoroacetic acid → HCID 58392393, compound

HRID 561631Notes

Reaction equation

HRID 561631 reaction equation
[Cl-].[In+3].[Cl-].[Cl-].FC(F)(F)C(O)=O.[CH2:12]([C:14]1(O)[C:22]2[C:17](=[CH:18][C:19]([F:23])=[CH:20][CH:21]=2)[CH2:16][CH2:15]1)[CH3:13].[CH3:25][S:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[C:32]2[C:36]=1[NH:35][CH:34]=[CH:33]2>ClCCl>[CH2:12]([C:14]1([C:33]2[C:32]3[C:36](=[C:28]([CH2:27][S:26][CH3:25])[CH:29]=[CH:30][CH:31]=3)[NH:35][CH:34]=2)[C:22]2[C:17](=[CH:18][C:19]([F:23])=[CH:20][CH:21]=2)[CH2:16][CH2:15]1)[CH3:13]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 159675indium(III)chlorideHCID 583921877-[(Methylsulfanyl)methyl]-1H-indoleHCID 593404281-Ethyl-5-fluoroindan-1-ol

Product 1

HCID 58392393HCID 58392393, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

515 mg (2.33 mmol) of indium(III) chloride and 0.17 ml (2.22 mmol) of trifluoroacetic acid were added to 400 mg (2.22 mmol) of the compound from Example 135A and 393 mg (2.22 mmol) of the compound from Example 8A in 12 ml of dichloromethane at 0° C., and the mixture was stirred at RT for 1 h. It was diluted with dichloromethane, washed with water, dried over magnesium sulfate, filtered and concentrated. The residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 33 mg (4% of theory) of the title compound as mixture of diastereomers.

Workup

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)

Sources & evidence

ORD record
ord-26cf422c4a244762a395df30998ab0cb
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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