Trifluoroacetic acid → 3-(5,7-Difluoro-4-methyl-3,4-dihydro-2H-chromen-4-yl)-7-[(methylsulfanyl)methyl]-1H-indole

HRID 561643Notes

Reaction equation

HRID 561643 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[C:4]([CH3:14])(O)[CH2:5][CH2:6][O:7]2.FC(F)(F)C(O)=O.[CH3:22][S:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[C:29]2[C:33]=1[NH:32][CH:31]=[CH:30]2>ClCCl>[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[C:4]([C:30]1[C:29]3[C:33](=[C:25]([CH2:24][S:23][CH3:22])[CH:26]=[CH:27][CH:28]=3)[NH:32][CH:31]=1)([CH3:14])[CH2:5][CH2:6][O:7]2

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 583921705,7-Difluoro-4-methyl-3,4-dihydro-2H-chromen-4-olHCID 583921877-[(Methylsulfanyl)methyl]-1H-indole

Product 1

HCID 583920983-(5,7-Difluoro-4-methyl-3,4-dihydro-2H-chromen-4-yl)-7-[(methylsulfanyl)methyl]-1H-indole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

565 mg (2.82 mmol) of the compound from Example 171A and 0.26 ml (3.39 mmol) of trifluoroacetic acid were added to 500 mg (2.82 mmol) of the compound from Example 8A in 20 ml of dichloromethane. The reaction mixture was stirred at RT for 30 min, the solvent was removed in vacuo, and the crude product was then purified by preparative HPLC (mobile phase: acetonitrile/water gradient) and subsequent flash chromatography on silica gel (mobile phase: dichloromethane). 632 mg (62% of theory) of the title compound were obtained.

Workup

  1. customthe solvent was removed in vacuo
  2. customthe crude product was then purified by preparative HPLC (mobile phase: acetonitrile/water gradient) and subsequent flash chromatography on silica gel (mobile phase: dichloromethane)

Sources & evidence

ORD record
ord-045a872f51894261811272af4c960035
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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