Trifluoroacetic acid → HCID 58392386, compound

HRID 561654Notes

Reaction equation

HRID 561654 reaction equation
FC(F)(F)C(O)=O.[CH:8]1([CH:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[F:23])O)[CH2:10][CH2:9]1.[CH3:24][S:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[C:31]2[C:35]=1[NH:34][CH:33]=[CH:32]2>ClCCl>[CH:8]1([CH:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[F:23])[C:32]2[C:31]3[C:35](=[C:27]([CH2:26][S:25][CH3:24])[CH:28]=[CH:29][CH:30]=3)[NH:34][CH:33]=2)[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 583921877-[(Methylsulfanyl)methyl]-1H-indoleHCID 58392553HCID 58392553, compound

Product 1

HCID 58392386HCID 58392386, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.66 ml (8.61 mmol) of trifluoroacetic acid was added to 1.68 g (7.18 mmol) of the compound from Example 148A and 1.27 g (7.18 mmol) of the compound from Example 8A in 80 ml of dichloromethane, and the mixture was stirred at RT for 2 h. It was concentrated and the residue was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate 98/2) and preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 80.0 mg (3% of theory) of the title compound.

Workup

  1. concentrationIt was concentrated
  2. customthe residue was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate 98/2) and preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)

Sources & evidence

ORD record
ord-fb23b2e1411e4937b03a869609974f6b
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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