Tert-Butylamine → N-tert-butyl-5-iodo-4-(2-(thiophen-3-yl)ethoxy)pyridin-2-amine

HRID 2078964Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2078964
C1(C)C=CC(S(OS(C2C=CC(C)=CC=2)(=O)=O)(=O)=O)=CC=1.[I:22][C:23]1[CH:24]=[N+:25]([O-])[CH:26]=[CH:27][C:28]=1[O:29][CH2:30][CH2:31][C:32]1[CH:36]=[CH:35][S:34][CH:33]=1.[C:38]([NH2:42])([CH3:41])([CH3:40])[CH3:39]>C(Cl)(Cl)Cl>[C:38]([NH:42][C:26]1[CH:27]=[C:28]([O:29][CH2:30][CH2:31][C:32]2[CH:36]=[CH:35][S:34][CH:33]=2)[C:23]([I:22])=[CH:24][N:25]=1)([CH3:41])([CH3:40])[CH3:39]

Komponenten

5

Edukt 3

HCID 6385Tert-Butylamine2×HCID 77773Toluene-p-sulphonic anhydride2×HCID 582840413-Iodo-4-(2-(thiophen-3-yl)ethoxy)pyridine 1-oxide

Produkt 1

HCID 57900152N-tert-butyl-5-iodo-4-(2-(thiophen-3-yl)ethoxy)pyridin-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

A solution of p-toluenesulfonic anhydride (1.47 g, 4.49 mmol) in 15 ml of chloroform was added dropwise to a stirred mixture of 0.78 g (2.25 mmol) of 3-iodo-4-(2-(thiophen-3-yl)ethoxy)pyridine 1-oxide and 1.18 ml (11.2 mmol) of tert-butylamine in 15 ml of chloroform at 0° C. After 30 minutes, the addition of the same quantities of p-toluenesulfonic anhydride and tert-butylamine was repeated to complete the reaction. The reaction mixture was concentrated and partitioned between 100 ml of diethylether and 1 M aqueous sodium carbonate. The aqueous layer was extracted with 50 ml of diethylether again and combined organic extracts were washed with water, brine, dried over sodium sulfate and concentrated in vacuum. The residue was purified by flash chromatography eluting with 10% of ethyl acetate in hexane to give N-tert-butyl-5-iodo-4-(2-(thiophen-3-yl)ethoxy)pyridin-2-amine (0.473 g (52%). 1H NMR (400 MHz, CDCl3) δ 8.15 (s, 1H), 7.28 (dd, J=3.0, 4.8, 1H), 7.18 (s, 1H), 7.12 (d, J=4.9, 1H), 5.85 (s, 1H), 4.44 (s, 1H), 4.15 (t, J=6.5, 2H), 3.18 (t, J=6.5, 2H), 1.39 (s, 9H). MS: (ESI+) 403.2

Aufarbeitung

  1. customthe reaction
  2. concentrationThe reaction mixture was concentrated
  3. custompartitioned between 100 ml of diethylether and 1 M aqueous sodium carbonate
  4. extractionThe aqueous layer was extracted with 50 ml of diethylether again
  5. washwere washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuum
  8. customThe residue was purified by flash chromatography
  9. washeluting with 10% of ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-c52013b8cd3f4fa2946bd7a95b285bc0
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07928248B2

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