Potassium Carbonate → HCID 86625879, Verbindung

HRID 2421991Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2421991
Cl[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[NH:13]1[CH2:16][CH:15]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:14]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:8][C:7]1[C:2]([N:13]2[CH2:16][CH:15]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[CH2:14]2)=[N:3][CH:4]=[C:5]([C:9]([F:12])([F:11])[F:10])[CH:6]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 1122342,3-Dichloro-5-(trifluoromethyl)pyridineHCID 15194053-Aminoazetidine, 3-BOC protected

Produkt 1

HCID 86625879HCID 86625879, VerbindungAusbeute 34,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

2,3-Dichloro-5-(trifluoromethyl)pyridine (1.50 g, 6.94 mmol), tert-butyl azetidin-3-ylcarbamate (1.67 g, 9.72 mmol) and K2CO3 (2.88 g, 20.83 mmol) were dissolved in dry DMF (13 mL) under nitrogen atmosphere. The reaction mixture was heated in a microwave reactor at 150° C. for 15 mins. The reaction mixture was filtered and diluted with EtOAc, washed with water, dried over MgSO4, filtered and evaporated. The crude product was purified by column chromatography (ISOLUTE SI (20 g), eluated with DCM, DCM/MeOH (99:1)) affording the title compound (0.85 g, 34.8%). 1H NMR (500 MHz, CDCl3): δ 1.48 (s, 9H), 4.10-4.14 (m, 2H), 4.57 (bs, 1H), 4.65 (t, 2H), 5.00 (bs, 1H), 7.61 (s, 1H), 8.28 (s, 1H); 13C NMR (125 MHz, CDCl3): δ 28.56, 41.67, 60.34, 80.45, 115.51, 117.44 (q, JC-F=33.2 Hz), 123.83 (m, JC-F=271.4 Hz), 135.06, 143.75, 155.18, 157.35; Mass Spectrum: M−H+ 350.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. additiondiluted with EtOAc
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by column chromatography (ISOLUTE SI (20 g), eluated with DCM, DCM/MeOH (99:1))

Quellen und Nachweise

ORD-Eintrag
ord-193495014f394378854c44ac9f3700d5
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960380B2

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