Trifluoroacetic acid → 3-[(2-Chloro-4-methylphenyl)(cyclopropyl)methyl]-7-[(methylsulfonyl)methyl]-1H-indole

HRID 561672Notes

Reaction equation

HRID 561672 reaction equation
[Cl-].[In+3].[Cl-].[Cl-].FC(F)(F)C(O)=O.[CH3:12][S:13]([CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[C:25]=1[NH:24][CH:23]=[CH:22]2)(=[O:15])=[O:14].[Cl:26][C:27]1[CH:32]=[C:31]([CH3:33])[CH:30]=[CH:29][C:28]=1[CH:34]([CH:36]1[CH2:38][CH2:37]1)O>ClCCl>[Cl:26][C:27]1[CH:32]=[C:31]([CH3:33])[CH:30]=[CH:29][C:28]=1[CH:34]([CH:36]1[CH2:38][CH2:37]1)[C:22]1[C:21]2[C:25](=[C:17]([CH2:16][S:13]([CH3:12])(=[O:15])=[O:14])[CH:18]=[CH:19][CH:20]=2)[NH:24][CH:23]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 159675indium(III)chlorideHCID 583922947-[(Methylsulfonyl)methyl]-1H-indoleHCID 583925292-Chloro-alpha-cyclopropyl-4-methylbenZenemethanol

Product 1

HCID 583924503-[(2-Chloro-4-methylphenyl)(cyclopropyl)methyl]-7-[(methylsulfonyl)methyl]-1H-indole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

135 mg (0.61 mmol) of indium(III) chloride and 0.07 ml (0.92 mmol) of trifluoroacetic acid were added to 132 mg (0.61 mmol) of the compound from Example 86A and 100 mg (0.51 mmol) of the compound from Example 152A in 5 ml of dichloromethane, and the mixture was stirred at RT overnight. It was concentrated and the residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 29.0 mg (15% of theory) of the title compound.

Workup

  1. concentrationIt was concentrated
  2. 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-7e272cd946594edfae16047ce995f66b
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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