Methyl N-(triethylammoniosulfonyl)carbamate → 2-Chloro-4-methoxy-6-(4-trifluoromethyl-thiazol-2-yl)-pyridine

HRID 530755Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 530755
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[S:9][CH2:10][C:11]([C:14]([F:17])([F:16])[F:15])(O)[N:12]=2)[CH:5]=[C:4]([O:18][CH3:19])[CH:3]=1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([O:18][CH3:19])[CH:5]=[C:6]([C:8]2[S:9][CH:10]=[C:11]([C:14]([F:17])([F:15])[F:16])[N:12]=2)[N:7]=1

Komponenten

4

Edukt 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 866691152-(6-Chloro-4-methoxy-pyridin-2-yl)-4-trifluoromethyl-4,5-dihydro-thiazol-4-ol

Produkt 1

HCID 866691142-Chloro-4-methoxy-6-(4-trifluoromethyl-thiazol-2-yl)-pyridineAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of compound 20 (8.67 mmol) in THF (30 mL) was added Burgess Reagent (9.5 mmol). The reaction mixture was stirred at 60° C. for 30 min. The solution was concentrated in vacuo and H2O and DCM were added. The layers were separated and the organic layer was concentrated. The crude was purified by silica gel chromatography (eluent: petroleum ether/DCM 50 to 100%) to give compound 21 as a beige solid in 48% yield. MS (ESI, EI+): m/z=294.87 (MH+).

Aufarbeitung

  1. concentrationThe solution was concentrated in vacuo and H2O and DCM
  2. additionwere added
  3. customThe layers were separated
  4. concentrationthe organic layer was concentrated
  5. customThe crude was purified by silica gel chromatography (eluent: petroleum ether/DCM 50 to 100%)

Quellen und Nachweise

ORD-Eintrag
ord-035de6ad101646ddb373b359051a1b1a
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353100B2

Notizen zur Reaktion

Wird geladen…