Trifluoroacetic acid → 3-[1-(4-Chlorophenyl)-1-cyclopropylethyl]-7-[(methylsulfanyl)methyl]-1H-indole

HRID 561634Notes

Reaction equation

HRID 561634 reaction equation
[CH:1]1([C:4]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)(O)[CH3:5])[CH2:3][CH2:2]1.FC(F)(F)C(O)=O.[CH3:21][S:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]2[C:32]=1[NH:31][CH:30]=[CH:29]2>ClCCl>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:4]([C:29]2[C:28]3[C:32](=[C:24]([CH2:23][S:22][CH3:21])[CH:25]=[CH:26][CH:27]=3)[NH:31][CH:30]=2)([CH:1]2[CH2:3][CH2:2]2)[CH3:5])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 234634-Chloro-alpha-cyclopropyl-alpha-methylbenzenemethanolHCID 583921877-[(Methylsulfanyl)methyl]-1H-indole

Product 1

HCID 583922903-[1-(4-Chlorophenyl)-1-cyclopropylethyl]-7-[(methylsulfanyl)methyl]-1H-indole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

600 mg (3.05 mmol) of the compound from Example 138A and 0.28 ml (3.66 mmol) of trifluoroacetic acid were added to 541 mg (3.05 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 three times by preparative HPLC (mobile phase: acetonitrile/water gradient) and once by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10/1). 441 mg (41% of theory) of the title compound were obtained.

Workup

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

Sources & evidence

ORD record
ord-715334ddb2494622b5c8a6c327cd4bfa
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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