(Trifluoromethyl)trimethylsilane → HCID 68551826, compound

HRID 1868144Notes

Reaction equation

HRID 1868144 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24](=[O:26])[CH3:25])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C@H:11]([CH3:27])[CH2:10]1.[Si]([C:32]([F:35])([F:34])[F:33])(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([OH:26])([CH3:25])[C:32]([F:35])([F:34])[F:33])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C@H:11]([CH3:27])[CH2:10]1

Participants

4

Reactant 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 68554748HCID 68554748, compound

Product 1

HCID 68551826HCID 68551826, compoundYield 81%

Procedure

To a solution of (R)-1-(4-(4-(2,4-difluorophenyl)-2-methylpiperazin-1-ylsulfonyl)phenyl)ethanone (360 mg, 0.87 mmol, prepared according to procedures similar to those described in Example 29A) was added TMSCF3 (5.2 mL, 0.5 M in THF, 2.6 mmol) and TBAF (0.87 mL, 1 M in THF, 1.0 mmol) at 0° C. The resultant mixture was stirred for 6 h then rt overnight. It washed with aq. NH4Cl and aq. layer was extracted with DCM. The organic layer was dried over Na2SO4. The crude product was purified on SiO2 column eluted with hexanes/EtOAc to give the desired product as a white solid (329 mg, 81%). HRMS: calcd for C20H21F5N2O3S+H+, 465.12658. found (ESI-FTMS, [M+H]1+), 465.12565.

Workup

  1. customrt overnight
  2. washIt washed with aq. NH4Cl and aq. layer
  3. extractionwas extracted with DCM
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customThe crude product was purified on SiO2 column
  6. washeluted with hexanes/EtOAc

Sources & evidence

ORD record
ord-c21c5e0479f742f0bd15f74c3c270717
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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