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tert-Butylsulfinamide, (R)-(+)- → (NE,R)-N-[1-(6-bromo-3-fluoro-4-triethylsilyl-2-pyridinyl)ethylidene]-2-methylpropane-2-sulfinamide

HRID 1752455
Notes
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Reaction equation

HRID 1752455 reaction equation
[C:1]([S@:5]([NH2:7])=[O:6])([CH3:4])([CH3:3])[CH3:2].[Br:8][C:9]1[N:14]=[C:13]([C:15](=O)[CH3:16])[C:12]([F:18])=[C:11]([Si:19]([CH2:24][CH3:25])([CH2:22][CH3:23])[CH2:20][CH3:21])[CH:10]=1>C1COCC1.[Cl-].[Na+].O>[Br:8][C:9]1[N:14]=[C:13](/[C:15](=[N:7]/[S@@:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[O:6])/[CH3:16])[C:12]([F:18])=[C:11]([Si:19]([CH2:22][CH3:23])([CH2:20][CH3:21])[CH2:24][CH3:25])[CH:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 866680691-(6-Bromo-3-fluoro-4-triethylsilanyl-pyridin-2-yl)-ethanone

Product 1

HCID 89415106(NE,R)-N-[1-(6-bromo-3-fluoro-4-triethylsilyl-2-pyridinyl)ethylidene]-2-methylpropane-2-sulfinamideYield 82%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent
HCID 57417360
Sodium chloride; water
Solvent

Procedure

A mixture of titantetraethoxide (4.26 g, 18.69 mmol), (R)-tert.-butylsulfinamide (1.246 g, 10.28 mmol) and 1-(6-bromo-3-fluoro-4-triethylsilanyl-pyridin-2-yl)-ethanone (3.45 g, 9.34 mmol, 90% pure) in THF (25 ml) was refluxed under a nitrogen atmosphere for 6 hours. The cold reaction mixture was poured onto icecold brine (200 ml) with gentle stirring. The precipitate was filtered through a pad of hyflo and washed with ethyl acetate. The filtrate was diluted with ethyl acetate and washed with brine, dried over sodium sulfate, filtered and evaporated. The crude yellow oil (4.55 g) was chromatographed over silica gel (cyclohexane/ethyl acetate 94:6) to give the title compound as a yellow oil. 3.35 g (82% yield).

Workup

  1. temperaturewas refluxed under a nitrogen atmosphere for 6 hours
  2. customThe cold reaction mixture
  3. filtrationThe precipitate was filtered through a pad of hyflo
  4. washwashed with ethyl acetate
  5. additionThe filtrate was diluted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe crude yellow oil (4.55 g) was chromatographed over silica gel (cyclohexane/ethyl acetate 94:6)

Sources & evidence

ORD record
ord-ddc46a001ae649c3bb20d4adc22e1618
Source dataset
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09163011B2

Reaction notes

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