Boron tribromide → Ethyl 1-(6-(2-hydroxy-5-methylphenyl)pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

HRID 1255174

Reaktionsgleichung

Reaktionsgleichung von HRID 1255174
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[C:10]1[N:15]=[C:14]([N:16]2[C:20]([C:21]([F:24])([F:23])[F:22])=[C:19]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:18]=[N:17]2)[CH:13]=[CH:12][CH:11]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[C:10]1[N:15]=[C:14]([N:16]2[C:20]([C:21]([F:24])([F:23])[F:22])=[C:19]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:18]=[N:17]2)[CH:13]=[CH:12][CH:11]=1

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 67159458Ethyl 1-[6-(2-methoxy-5-methylphenyl)pyridin-2-yl]-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

Produkt 1

HCID 136017878Ethyl 1-(6-(2-hydroxy-5-methylphenyl)pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a cooled (0° C.) solution of the title compound from Example 8 Step A in DCM (20 mL) was added boron tribromide (11.7 mL, 1.0 M in DCM, 11.7 mmol). After 15 min, the reaction mixture was allowed to warm to ambient temperature. After an additional 2 h, the reaction mixture was cooled to 0° C., then was quenched by dropwise addition of sat. aq. NaHCO3 (gas evolution) and was extracted with DCM. The organic phase was separated and concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 30% EtOAc in hexanes, then 30 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 392.6 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 11.78 (s, 1H), 8.17 (s, 1H), 8.07-8.03 (m, 2H), 7.60 (d, J=1.5 Hz, 1H), 7.48 (dd, J=7.0, 1.5 Hz, 1H), 7.17 (dd, J=8.0, 2.0 Hz, 1H), 6.94 (d, J=8.0 Hz, 1H), 4.39 (q, J=7.0 Hz, 2H), 2.36 (s, 3H), 1.40 (t, J=7.0 Hz, 3H).

Aufarbeitung

  1. waitAfter an additional 2 h
  2. temperaturethe reaction mixture was cooled to 0° C.
  3. customwas quenched by dropwise addition of sat. aq. NaHCO3 (gas evolution)
  4. extractionwas extracted with DCM
  5. customThe organic phase was separated
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography on silica gel (0 to 30% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-62703420f2704a4a94fe1e10e648a211
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455638B2

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