Hydrochloric Acid → (5-Bromo-pyridin-2-yl)-(6-trifluoromethyl-pyridin-3-yl)-amine

HRID 1404235

Reaktionsgleichung

Reaktionsgleichung von HRID 1404235
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([F:11])([F:10])[F:9])=[N:6][CH:7]=1.[Br:12][C:13]1[CH:14]=[CH:15][C:16](F)=[N:17][CH:18]=1.Cl>C(O)CCC>[Br:12][C:13]1[CH:14]=[CH:15][C:16]([NH:1][C:2]2[CH:7]=[N:6][C:5]([C:8]([F:11])([F:9])[F:10])=[CH:4][CH:3]=2)=[N:17][CH:18]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 27377445-Amino-2-(trifluoromethyl)pyridineHCID 27831685-Bromo-2-fluoropyridine

Produkt 1

HCID 66615754(5-Bromo-pyridin-2-yl)-(6-trifluoromethyl-pyridin-3-yl)-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 5-amino-2-(trifluoromethyl)pyridine (0.5 g, 3.0 mmol, 1.0 equiv) and 5-bromo-2-fluoropyridine (0.47 mL, 4.6 mmol, 1.5 equiv) in 2 mL 1-butanol was charged with 0.15 mL of 4.0 M HCl (in dioxane) and heated to 150° C. via microwave heating. After cooling to room temperature, the reaction mixture was partitioned between ethyl acetate and saturated bicarbonate, and the organic extracts were washed with brine and dried over sodium sulphate. Purification of the crude product by flash chromatography afforded the title compound: 1H NMR (400 MHz, CDCl3) δ 6.63 (br. s., 1 H) 6.67 (d, J=9.35 Hz, 1 H) 7.56 (d, J=8.59 Hz, 1 H) 7.62 (dd, J=8.84, 2.53 Hz, 1 H) 8.22-8.66 (m, 2 H) 8.57 (d, J=2.78 Hz, 1 H); (M+H)+ 320.0.

Aufarbeitung

  1. temperatureheating
  2. temperatureAfter cooling to room temperature
  3. customthe reaction mixture was partitioned between ethyl acetate and saturated bicarbonate
  4. washthe organic extracts were washed with brine
  5. dry with materialdried over sodium sulphate
  6. customPurification of the crude product by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-27efc71cf9af4db888bce4b80eaa02b6
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08912208B2

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