Cesium carbonate → Ethyl 1-(6-{2-[(4-bromobenzyl)oxy]phenyl}pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

HRID 1255162

Reaktionsgleichung

Reaktionsgleichung von HRID 1255162
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]([N:14]2[C:18]([C:19]([F:22])([F:21])[F:20])=[C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:16]=[N:15]2)[CH:11]=[CH:10][CH:9]=1.[Br:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33]Br)=[CH:31][CH:30]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH4+].[Cl-]>CN(C=O)C>[Br:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[C:8]2[N:13]=[C:12]([N:14]3[C:18]([C:19]([F:22])([F:21])[F:20])=[C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:16]=[N:15]3)[CH:11]=[CH:10][CH:9]=2)=[CH:31][CH:30]=1

Komponenten

6

Edukt 4

HCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 685274-Bromobenzyl bromideHCID 136298134Ethyl 1-[6-(2-hydroxylphenyl)pyridine-2-yl]-5-trifluoromethyl-1H-pyrazole-4-carboxylate

Produkt 1

HCID 67159752Ethyl 1-(6-{2-[(4-bromobenzyl)oxy]phenyl}pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of the title compound from Example 1 Step B (682 mg, 1.81 mmol) in DMF (10 mL) were added 4-bromobenzyl bromide (678 mg, 2.71 mmol) and cesium carbonate (1.77 g, 5.42 mmol). After 1.5 h, the reaction mixture was poured into sat. aq. NH4Cl and extracted with EtOAc. The organic phase was separated, dried over sodium sulfate, filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 25% EtOAc in hexanes, then 25 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 548.0 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.13 (s, 1H), 8.08 (d, J=8.0 Hz, 1H), 7.95 (dd, J=7.5, 1.5 Hz, 1H), 7.88 (t, J=8.0 Hz, 1H), 7.54 (d, J=8.0 Hz, 1H), 7.48 (d, J=8.0 Hz, 2H), 7.39-7.36 (m, 1H), 7.23 (d, J=8.0 Hz, 2H), 7.12 (t, J=7.5 Hz, 1H), 7.03 (d, J=7.5 Hz, 1H), 5.10 (s, 2H), 4.39 (q, J=7.0 Hz, 2H), 1.39 (t, J=7.0 Hz, 3H).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. customThe organic phase was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica gel (0 to 25% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-c5bf0cddcda54265b0984b03cc8637df
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455638B2

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