(Trifluoromethyl)trimethylsilane → HCID 86691229, compound

HRID 880223Notes

Reaction equation

HRID 880223 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 min. Add saturated aqueous ammonium chloride solution (1.2 L) and extract with EtOAc (4×400 mL). Combine the extracts and sequentially wash the extracts 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 reduced pressure 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 extracts and sequentially wash the extracts 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. customdry the filtrate under reduced pressure

Sources & evidence

ORD record
ord-054a73751cd7471b970a90125b990b4e
Source dataset
uspto-grants-2015_03
Patent number
US08993568B2

Reaction notes

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