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Triethylamine → 4-(3-bromo-5-(5-(trifluoromethyl)pyridin-2-yloxy)benzylidene)-N-(pyridin-3-yl)piperidine-1-carboxamide

HRID 1666462
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1666462
[Br:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([CH:19]=[C:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[CH:18]=1)[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][N:7]=1.[N:26]1[CH:31]=[CH:30][CH:29]=[C:28]([NH:32][C:33](=O)[O:34]C2C=CC=CC=2)[CH:27]=1.C(N(CC)CC)C>CS(C)=O.O>[Br:1][C:2]1[CH:18]=[C:17]([CH:16]=[C:4]([O:5][C:6]2[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][N:7]=2)[CH:3]=1)[CH:19]=[C:20]1[CH2:25][CH2:24][N:23]([C:33]([NH:32][C:28]2[CH:27]=[N:26][CH:31]=[CH:30][CH:29]=2)=[O:34])[CH2:22][CH2:21]1
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Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 6935890Phenyl pyridin-3-ylcarbamateHCID 668769892-(3-Bromo-5-(piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridine

Produkt 1

HCID 249679954-(3-bromo-5-(5-(trifluoromethyl)pyridin-2-yloxy)benzylidene)-N-(pyridin-3-yl)piperidine-1-carboxamideAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679
Dimethyl Sulfoxide
Lösungsmittel
HCID 962WaterLösungsmittel

Versuchsvorschrift

2-(3-Bromo-5-(piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridine (0.58 g, 1.4 mmol) and phenyl pyridin-3-ylcarbamate (0.3 g, 1.4 mmol) were dissolved in DMSO (3 mL). Triethylamine (0.59 mL, 4.21 mmol) was added and the reaction was stirred overnight. The reaction mixture was diluted with water and extracted with ethyl acetate three times. The organic layer was washed with brine, dried over Na2SO4, and evaporated to dryness. The residue was purified by silica gel column chromatography (35% acetone in hexane) to give the title compound (0.5 g, 67%). 1H NMR (500 MHz, DMSO-d6): δ 8.44 (s, 2H), 8.25 (d, J=4.4 Hz, 1H), 7.99 (d, J=7.8 Hz, 1H), 7.92 (d, J=10.45 Hz, 1H), 7.22 (m, 2H), 7.20 (s, 1H), 7.04 (d, J=8.6 Hz, 1H), 6.93 (s, 1H), 6.83 (s, 1H), 6.34 (s, 1H), 3.60 (m, 2H), 3.52 (m, 2H), 2.56 (m, 2H), 2.44 (m, 2H). 13C NMR (125 MHz, CDCl3): δ 165.16, 154.72, 153.51, 145.38, 143.81, 141.22, 140.33, 139.66, 136.99, 136.36, 128.85, 127.64, 123.63, 123.26, 122.83, 122.48, 120.73, 111.68, 45.59, 44.60, 35.71, 29.29, 29.17; m/z (533.2, 535.2, M+ H+); HPLC: 99.0%.

Aufarbeitung

  1. extractionextracted with ethyl acetate three times
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness
  5. customThe residue was purified by silica gel column chromatography (35% acetone in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-547a9507579a42c2b5bde770ec4fc592
Quelldatensatz
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08044052B2

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