(Trifluoromethyl)trimethylsilane → HCID 86691229, compound

HRID 1518949Notes

Reaction equation

HRID 1518949 reaction equation
[F:1][C:2]([Si](C)(C)C)([F:4])[F:3].[Br:9][C:10]1[CH:15]=[CH:14][C:13](/[CH:16]=[N:17]\[S@@:18]([C:20]([CH3:23])([CH3:22])[CH3:21])=[O:19])=[CH:12][CH:11]=1>C([O-])(=O)C.C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[Br:9][C:10]1[CH:11]=[CH:12][C:13]([C@H:16]([NH:17][S@@:18]([C:20]([CH3:23])([CH3:22])[CH3:21])=[O:19])[C:2]([F:4])([F:3])[F:1])=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 89713970HCID 89713970, compound

Product 1

HCID 86691229HCID 86691229, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 82707Tetrabutylammonium AcetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
2.5 °C

Procedure

Add neat (trifluoromethyl)trimethylsilane (109 mL, 0.74 mol) at 0° C. to a stirred solution of tetrabutylammonium acetate (88 g, 0.29 mol) and (N—Z)—N-[(4-bromophenyl)methylene]-(R)-2-methyl-propane-2-sulfinamide (85 g, 0.29 mol) in dimethylformamide (1.2 L) at 0° C. Stir the mixture at 0-5° C. for 90 minutes. Add saturated aqueous ammonium chloride solution (1.2 L) and extract with EtOAc (4×400 mL). Combine and sequentially wash the organic phase with water then brine (2×1 L); dry over magnesium sulphate; filter; and concentrate the filtrate under vacuum. Triturate the residue with hexane (200 mL) for 10 minutes, filter and dry the filtrate under vacuum to afford the title compound as a yellow solid (81 g, 76% yield, >98 de). MS (m/z): 358 (M+1).

Workup

  1. extractionAdd saturated aqueous ammonium chloride solution (1.2 L) and extract with EtOAc (4×400 mL)
  2. washCombine and sequentially wash the organic phase with water
  3. dry with materialdry over magnesium sulphate
  4. filtrationfilter
  5. concentrationand concentrate the filtrate under vacuum
  6. customTriturate the residue with hexane (200 mL) for 10 minutes
  7. filtrationfilter
  8. customdry the filtrate under vacuum

Sources & evidence

ORD record
ord-462489dbc1884f00b7098c8b238bedc6
Source dataset
uspto-grants-2015_07
Patent number
US09073856B2

Reaction notes

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