Trifluoroacetic acid → 3-[1-(1-Benzothiophen-5-yl)-1-cyclopropylethyl]-7-[(methylsulfanyl)methyl]-1H-indole

HRID 561637Notes

Reaction equation

HRID 561637 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([CH:13]3[CH2:15][CH2:14]3)(O)[CH3:11])=[CH:9][C:4]=2[CH:3]=[CH: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>[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([C:31]3[C:30]4[C:34](=[C:26]([CH2:25][S:24][CH3:23])[CH:27]=[CH:28][CH:29]=4)[NH:33][CH:32]=3)([CH:13]3[CH2:15][CH2:14]3)[CH3:11])=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 583921221-(1-Benzothiophen-5-yl)-1-cyclopropylethanolHCID 583921877-[(Methylsulfanyl)methyl]-1H-indole

Product 1

HCID 583924583-[1-(1-Benzothiophen-5-yl)-1-cyclopropylethyl]-7-[(methylsulfanyl)methyl]-1H-indole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

600 mg (2.75 mmol) of the compound from Example 141A and 0.25 ml (3.30 mmol) of trifluoroacetic acid were added to 487 mg (2.75 mmol) of the compound from Example 8A in 4 ml of dichloromethane. The reaction mixture was stirred at RT for 30 min, and the crude product was then purified twice by preparative HPLC (mobile phase: acetonitrile/water gradient) and once by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10/1). 404 mg (39% of theory) of the title compound were obtained.

Workup

  1. customthe crude product was then purified twice by preparative HPLC (mobile phase: acetonitrile/water gradient) and once by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10/1)

Sources & evidence

ORD record
ord-f7da145f23dc4b49b41598d46ffc23b8
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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