(Trifluoromethyl)trimethylsilane → HCID 86691229, compound

HRID 2038214Notes

Reaction equation

HRID 2038214 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=O)C>[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 DMF (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 the organic extracts and sequentially wash with water then brine (2×1 L); dry over magnesium sulphate; filter; and concentrate the filtrate under reduced pressure. 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 the organic extracts and sequentially wash with water
  3. dry with materialdry over magnesium sulphate
  4. filtrationfilter
  5. concentrationand concentrate the filtrate under reduced pressure
  6. customTriturate the residue with hexane (200 mL) for 10 minutes
  7. filtrationfilter
  8. customand dry the filtrate under vacuum

Sources & evidence

ORD record
ord-800e1343c4a04422b61ee434eeec3f0f
Source dataset
uspto-grants-2013_11
Patent number
US08575352B2

Reaction notes

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