Trifluoroacetic acid → 3-[(4-Chlorophenyl)(cyclopropyl)methyl]-5-fluoro-7-[(methylsulfonyl)methyl]-1H-indole

HRID 561675Notes

Reaction equation

HRID 561675 reaction equation
[CH:1]1([CH:4]([C:6]2[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=2)O)[CH2:3][CH2:2]1.FC(F)(F)C(O)=O.[F:20][C:21]1[CH:22]=[C:23]2[C:27](=[C:28]([CH2:30][S:31]([CH3:34])(=[O:33])=[O:32])[CH:29]=1)[NH:26][CH:25]=[CH:24]2>ClCCl>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([CH:4]([CH:1]2[CH2:3][CH2:2]2)[C:24]2[C:23]3[C:27](=[C:28]([CH2:30][S:31]([CH3:34])(=[O:32])=[O:33])[CH:29]=[C:21]([F:20])[CH:22]=3)[NH:26][CH:25]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 866794-Chloro-alpha-cyclopropylbenzenemethanolHCID 583923185-Fluoro-7-[(methylsulfonyl)methyl]-1H-indole

Product 1

HCID 583922023-[(4-Chlorophenyl)(cyclopropyl)methyl]-5-fluoro-7-[(methylsulfonyl)methyl]-1H-indole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

64 mg (0.35 mmol) of the compound from Example 153A and 0.03 ml (0.42 mmol) of trifluoroacetic acid were added to 80 mg (0.35 mmol) of the compound from Example 87A in 2.5 ml of dichloromethane. The reaction mixture was stirred at RT for 45 min, the solvent was removed in vacuo, and the crude product was then purified by preparative HPLC (mobile phase: acetonitrile/water gradient). 110 mg (80% of theory) of the title compound were obtained.

Workup

  1. customthe solvent was removed in vacuo
  2. customthe crude product was then purified by preparative HPLC (mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-7f26d019e75b41eca4de21487de82cf5
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

Loading…