Cesium fluoride → HCID 71295612, compound

HRID 1776847Notes

Reaction equation

HRID 1776847 reaction equation
[Br:1][C:2]1[CH:21]=[CH:20][C:5]2[O:6][CH2:7][C:8](=[O:19])[CH2:9][N:10]3[C:18]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[CH:12]=[C:11]3[C:4]=2[CH:3]=1.[Si]([C:26]([F:29])([F:28])[F:27])(C)(C)C.[F-].[Cs+]>COCCOC.CCCC[N+](CCCC)(CCCC)CCCC.[F-].O>[Br:1][C:2]1[CH:21]=[CH:20][C:5]2[O:6][CH2:7][C:8]([C:26]([F:29])([F:28])[F:27])([OH:19])[CH2:9][N:10]3[C:18]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[CH:12]=[C:11]3[C:4]=2[CH:3]=1

Participants

7

Reactant 3

HCID 25953Cesium fluorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 71295500HCID 71295500, compound

Product 1

HCID 71295612HCID 71295612, compoundYield 55.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

A mixture of 2-bromo-6H-benzo[2,3][1,5]oxazocino[5,4-a]indol-7(8H)-one (60 mg, 0.18 mmol), TMSCF3 (275 mg, 0.194 mmol) and CsF (3 mg, 0.018 mmol) in DME (1 mL) was stirred at room temperature for 3 hours. The mixture was then diluted with TBAF (5 mL) and stirred for 1 hour at room temperature. The mixture was then diluted with water (25 mL) and extracted with ethyl acetate (20 mL×3). The organic layer was washed with brine (20 mL×2), dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified using prep-TLC (petroleum ether:EA=3:1) to provide 2-bromo-7-(trifluoromethyl)-7,8-dihydro-6H-benzo[2,3][1,5]oxazocino[5,4-a]indol-7-ol (40 mg, yield: 55.6%). MS (M+H)+: 412/414.

Workup

  1. stirringstirred for 1 hour at room temperature
  2. extractionextracted with ethyl acetate (20 mL×3)
  3. washThe organic layer was washed with brine (20 mL×2)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified

Sources & evidence

ORD record
ord-5e080db3b9824acaab8a5449012e192f
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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