Trifluoroacetic acid → 3-[1-Cyclopropyl-1-(3-fluoro-4-methoxyphenyl)ethyl]-7-[(methylsulfanyl)methyl]-1H-indole

HRID 561636Notes

Reaction equation

HRID 561636 reaction equation
[CH:1]1([C:4]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([F:15])[CH:8]=2)(O)[CH3:5])[CH2:3][CH2:2]1.FC(F)(F)C(O)=O.[CH3:23][S:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[C:30]2[C:34]=1[NH:33][CH:32]=[CH:31]2>ClCCl>[CH:1]1([C:4]([C:31]2[C:30]3[C:34](=[C:26]([CH2:25][S:24][CH3:23])[CH:27]=[CH:28][CH:29]=3)[NH:33][CH:32]=2)([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([F:15])[CH:8]=2)[CH3:5])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 583921877-[(Methylsulfanyl)methyl]-1H-indoleHCID 583922231-Cyclopropyl-1-(3-fluoro-4-methoxyphenyl)ethanol

Product 1

HCID 583923303-[1-Cyclopropyl-1-(3-fluoro-4-methoxyphenyl)ethyl]-7-[(methylsulfanyl)methyl]-1H-indole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

100 mg (0.48 mmol) of the compound from Example 140A and 0.04 ml (0.57 mmol) of trifluoroacetic acid were added to 84 mg (0.48 mmol) of the compound from Example 8A in 2.5 ml of dichloromethane. The reaction mixture was stirred at RT for 30 min, and the crude product was then purified directly by preparative HPLC (mobile phase: acetonitrile/water gradient). 63 mg (361% of theory) of the title compound were obtained.

Workup

  1. customthe crude product was then purified directly by preparative HPLC (mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-b8055f704b7e478a9388499ba44c2a2d
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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