Trifluoroacetic acid → [6-Bromo-1-(2-hydroxy-ethyl)-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(4-cyclopropanesulfonyl-piperazin-1-yl)-methanone

HRID 1786462Notes

Reaction equation

HRID 1786462 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:21]([N:23]3[CH2:28][CH2:27][N:26]([S:29]([CH:32]4[CH2:34][CH2:33]4)(=[O:31])=[O:30])[CH2:25][CH2:24]3)=[O:22])[N:8]2[CH2:11][CH2:12][O:13][Si](C(C)(C)C)(C)C)=[CH:4][C:3]=1[O:35][CH:36]1[CH2:41][CH2:40][N:39]([CH:42]([CH3:44])[CH3:43])[CH2:38][CH2:37]1.FC(F)(F)C(O)=O>ClCCl>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:21]([N:23]3[CH2:28][CH2:27][N:26]([S:29]([CH:32]4[CH2:34][CH2:33]4)(=[O:30])=[O:31])[CH2:25][CH2:24]3)=[O:22])[N:8]2[CH2:11][CH2:12][OH:13])=[CH:4][C:3]=1[O:35][CH:36]1[CH2:37][CH2:38][N:39]([CH:42]([CH3:44])[CH3:43])[CH2:40][CH2:41]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68566693[6-bromo-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(4-cyclopropanesulfonyl-piperazin-1-yl)-methanone

Product 1

HCID 68566618[6-Bromo-1-(2-hydroxy-ethyl)-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(4-cyclopropanesulfonyl-piperazin-1-yl)-methanoneYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 85 mg (0.12 mmol) [6-bromo-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(4-cyclopropanesulfonyl-piperazin-1-yl)-methanone in 2 mL dichloromethane was cooled to 0° C. and 1.0 mL (1.49 g, 13.1 mmol) trifluoroacetic acid were added. The cooling bath was removed and after stirring for 1 h at room temperature the solution was evaporated to dryness. The residue was taken up in dichloromethane and extracted with 1M aqueous sodium hydroxide solution. The organic layer was washed with brine, dried over magnesium sulfate, filtered and evaporated to afford 71 mg (99%) of the title compound as colourless oil.

Workup

  1. customThe cooling bath was removed
  2. customwas evaporated to dryness
  3. extractionextracted with 1M aqueous sodium hydroxide solution
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-5cd740228ca8414e86fd02cc422b5198
Source dataset
uspto-grants-2009_03
Patent number
US07507736B2

Reaction notes

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