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Triethylamine → tert-butyl 3-(1-benzyl-1H-pyrazol-4-yl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 659637
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 659637
FC(F)(F)S(O[C:7]1[CH2:8][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10][CH2:11][CH:12]=1)(=O)=O.[CH2:22]([N:29]1[CH:33]=[C:32](B2OC(C)(C)C(C)(C)O2)[CH:31]=[N:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1.C(O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:22]([N:29]1[CH:33]=[C:32]([C:7]2[CH2:8][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10][CH2:11][CH:12]=2)[CH:31]=[N:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 3

HCID 8471TriethylamineHCID 27347711-Benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 53978067tert-Butyl 3-(((trifluoromethyl)sulfonyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate

Produkt 1

HCID 67997011tert-butyl 3-(1-benzyl-1H-pyrazol-4-yl)-5,6-dihydropyridine-1(2H)-carboxylateAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 702EthanolLösungsmittel
HCID 962WaterLösungsmittel2×
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A 250-mL 3-necked round-bottomed flask was charged with a solution of tert-butyl 3-(trifluoromethylsulfonyloxy)-5,6-dihydropyridine-1(2H)-carboxylate (5.0 g, 15.11 mmol, 1.00 equiv) in toluene (100 mL), a solution of 1-benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (4.29 g, 15.11 mmol, 1.00 equiv) in ethanol (100 mL), triethylamine (4.58 g, 45.35 mmol, 3.00 equiv), Pd(PPh3)4 (345 mg, 0.30 mmol, 0.01 equiv) and water (30 mL). The resulting mixture was heated to reflux for 3 hours. Upon completion, the mixture was diluted with water (100 mL). Then, it was extracted with ethyl acetate (3×200 mL). Combined organic layers were dried over anhydrous sodium sulfate and concentrated on a rotary evaporator. The residue was purified by silica gel column chromatography eluted with ethyl acetate/petroleum ether (1:5) affording tert-butyl 3-(1-benzyl-1H-pyrazol-4-yl)-5,6-dihydropyridine-1(2H)-carboxylate as yellow oil (5.0 g, 98%).

Aufarbeitung

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 3 hours
  3. extractionThen, it was extracted with ethyl acetate (3×200 mL)
  4. dry with materialCombined organic layers were dried over anhydrous sodium sulfate
  5. concentrationconcentrated on a rotary evaporator
  6. customThe residue was purified by silica gel column chromatography
  7. washeluted with ethyl acetate/petroleum ether (1:5)

Quellen und Nachweise

ORD-Eintrag
ord-b8d32d5b00974c9288c4fc6f138fa45e
Quelldatensatz
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08080566B1

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