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

HRID 561639Notes

Reaction equation

HRID 561639 reaction equation
[O: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[O: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>[O: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[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 583921877-[(Methylsulfanyl)methyl]-1H-indoleHCID 583922611-(Benzo[d][1,3]dioxol-5-yl)-1-cyclopropylethanol

Product 1

HCID 583921043-[1-(1,3-Benzodioxol-5-yl)-1-cyclopropylethyl]-7-[(methylsulfanyl)methyl]-1H-indole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

600 mg (2.91 mmol) of the compound from Example 143A and 0.27 ml (3.49 mmol) of trifluoroacetic acid were added to 516 mg (2.91 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). 377 mg (35% 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)

Sources & evidence

ORD record
ord-b39efd6c2e4c453c85a7af5b4ce8b073
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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