Triethylamine → (S)-Ethyl [N-({5-[(3-hydroxyphenyl)ethynyl]pyridin-3-yl}carbonyl)-S-phenylsulfonimidoyl]acetate

HRID 1099659

Reaktionsgleichung

Reaktionsgleichung von HRID 1099659
Br[C:2]1[CH:3]=[C:4]([C:8]([N:10]=[S:11]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:12])=[O:9])[CH:5]=[N:6][CH:7]=1.[OH:25][C:26]1[CH:27]=[C:28]([C:32]#[CH:33])[CH:29]=[CH:30][CH:31]=1.C(N(CC)CC)C>CN(C=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[OH:25][C:26]1[CH:27]=[C:28]([C:32]#[C:33][C:2]2[CH:3]=[C:4]([C:8]([N:10]=[S@:11]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:12])=[O:9])[CH:5]=[N:6][CH:7]=2)[CH:29]=[CH:30][CH:31]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 139144m-EthynylphenolHCID 76585243ethyl {N-[(5-bromopyridin-3-yl)carbonyl]-S-phenylsulfonimidoyl}acetate

Produkt 1

HCID 24954917(S)-Ethyl [N-({5-[(3-hydroxyphenyl)ethynyl]pyridin-3-yl}carbonyl)-S-phenylsulfonimidoyl]acetateAusbeute 94,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11776TriphenylphosphineKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution ethyl {N-[(5-bromopyridin-3-yl)carbonyl]-S-phenylsulfonimidoyl}acetate (216 mg, 0.52 mmol) and 3-hydroxyphenylacetylene (0.052 mL, 0.79 mmol) in anhydrous DMF (3 mL) was treated with triethylamine (0.22 mL, 1.58 mmol). The reaction mixture was degassed (alternating vacuum and argon) and PdCl2(Ph3P)2 (36.9 mg, 0.052 mmol) and triphenylphosphine (3.4 mg, 0.013 mmol) were added. The reaction mixture was degassed (alternating vacuum and argon) and placed under an atmosphere of 1:3 Argon/hydrogen atmosphere. Copper(1+) iodide was added and the reaction mixture was heated at 60° C. for 50 min. The brown reaction mixture was partitioned between saturated aqueous NaHCO3 and EtOAc. The organic layer was collected and washed further with saturated aqueous NaHCO3 (1×), brine (1×), and dried over anhydrous Na2SO4. The residue was purified by chromatography (silica gel, 50:1 CHCl3:MeOH). The product containing fractions were concentrated to give the title compound as a light yellow solid (220 mg, 94%).

Aufarbeitung

  1. additionwere added
  2. customThe reaction mixture was degassed (alternating vacuum and argon)
  3. additionCopper(1+) iodide was added
  4. customThe brown reaction mixture was partitioned between saturated aqueous NaHCO3 and EtOAc
  5. customThe organic layer was collected
  6. washwashed further with saturated aqueous NaHCO3 (1×), brine (1×)
  7. dry with materialdried over anhydrous Na2SO4
  8. customThe residue was purified by chromatography (silica gel, 50:1 CHCl3:MeOH)
  9. additionThe product containing fractions
  10. concentrationwere concentrated

Quellen und Nachweise

ORD-Eintrag
ord-6e6a6fd1f26b404b96e6248ed25dcd75
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143410B2

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