Trifluoroacetic acid → [6-Bromo-1-(2-hydroxy-ethyl)-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(1,1-dioxo-1lambda6-thiomorpholin-4-yl)-methanone

HRID 494001Notes

Reaction equation

HRID 494001 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][S:26](=[O:30])(=[O:29])[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:31][CH:32]1[CH2:37][CH2:36][N:35]([CH:38]([CH3:40])[CH3:39])[CH2:34][CH2:33]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[CH2:24][CH2:25][S:26](=[O:30])(=[O:29])[CH2:27][CH2:28]3)=[O:22])[N:8]2[CH2:11][CH2:12][OH:13])=[CH:4][C:3]=1[O:31][CH:32]1[CH2:37][CH2:36][N:35]([CH:38]([CH3:40])[CH3:39])[CH2:34][CH2:33]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67073382[6-Bromo-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(1,1-dioxo-1lambda6-thiomorpholin-4-yl)-methanone

Product 1

HCID 16739676[6-Bromo-1-(2-hydroxy-ethyl)-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(1,1-dioxo-1lambda6-thiomorpholin-4-yl)-methanoneYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of [6-bromo-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(1,1-dioxo-1λ6-thiomorpholin-4-yl)-methanone (130 mg, 1.0 eq.) and trifluoroacetic acid in dichloromethane was stirred for 1 h at room temperature and concentrated in vacuo. The crude mixture was partitioned between an aqueous solution of sodium hydroxide and dichloromethane. The aqueous layer was extracted with dichloromethane. Combined organic layers were washed with brine, dried over sodium sulfate, filtered and evaporated in vacuo, to yield 106 mg (99%) of the desired product as white foam. MS (m/e): 542.1 (M+H, 100%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe crude mixture was partitioned between an aqueous solution of sodium hydroxide and dichloromethane
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. washCombined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-38778f87b7d6432bb6e252e01981ab38
Source dataset
uspto-grants-2009_05
Patent number
US07538101B2

Reaction notes

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