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

HRID 561633

Reaction equation

HRID 561633 reaction equation
FC(F)(F)C(O)=O.[CH3:8][S:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:19]=1[NH:18][CH:17]=[CH:16]2.[CH:20]1([C:23]([C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)(O)[CH3:24])[CH2:22][CH2:21]1>ClCCl>[CH:20]1([C:23]([C:16]2[C:15]3[C:19](=[C:11]([CH2:10][S:9][CH3:8])[CH:12]=[CH:13][CH:14]=3)[NH:18][CH:17]=2)([C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)[CH3:24])[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 98258alpha-Cyclopropyl-alpha,4-dimethylbenzenemethanolHCID 583921877-[(Methylsulfanyl)methyl]-1H-indole

Product 1

HCID 583922803-[1-Cyclopropyl-1-(4-methylphenyl)ethyl]-7-[(methylsulfanyl)methyl]-1H-indole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.23 ml (3.00 mmol) of trifluoroacetic acid was added to 885 mg (4.99 mmol) of the compound from Example 8A and 440 mg (2.50 mmol) of the compound from Example 137A in 44 ml of dichloromethane, and the mixture was stirred at RT overnight. The reaction mixture was concentrated in a rotary evaporator. The residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 87.4 mg (10% of theory) of the title compound as mixture of diastereomers.

Workup

  1. concentrationThe reaction mixture was concentrated in a rotary evaporator
  2. customThe residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)

Sources & evidence

ORD record
ord-4da1d5476b2e4fe384010306eb100e3c
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Linked notes

Loading…