Diisopropylethylamine → 2-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)thiazol-2-yloxy)pyridine

HRID 1893716Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1893716
Br[C:2]1[N:3]=[C:4]([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[S:5][CH:6]=1.[CH3:14][O:15][C:16]1[CH:36]=[CH:35][C:19]([CH2:20][N:21]2[CH:25]=[C:24](B3OC(C)(C)C(C)(C)O3)[CH:23]=[N:22]2)=[CH:18][CH:17]=1.C(N(C(C)C)C(C)C)C>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:14][O:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:20][N:21]2[CH:25]=[C:24]([C:2]3[N:3]=[C:4]([O:7][C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=4)[S:5][CH:6]=3)[CH:23]=[N:22]2)=[CH:35][CH:36]=1

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 534402131-(4-methoxybenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 668718162-(4-Bromothiazol-2-yloxy)pyridine

Produkt 1

HCID 668891372-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)thiazol-2-yloxy)pyridineAusbeute 14,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 218864351,4-Dioxane--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

According to Scheme 3, Step 3: A mixture of 2-(4-bromothiazol-2-yloxy)pyridine (1.56 mmol, 400 mg), 1-(4-methoxybenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.87 mmol, 587 mg), PdCl2(dppf) (0.16 mmol, 127 mg) and N-ethyl-N-isopropylpropan-2-amine (3.11 mmol, 0.53 mL) in dioxane/water (1:1, 10 mL) was stirred at 150° C. for 1 hour under microwave conditions. The reaction mixture was filtered through a pad of celite and was washed with DCM. The organic phase was washed with water, was dried over MgSO4, was filtered and was concentrated under reduced pressure. The crude mixture was purified by flash chromatography over silica gel using cyclohexane/EtOAc (90:10 to 70:30) as eluent to yield 2-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)thiazol-2-yloxy)pyridine (0.23 mmol, 83 mg, 9%) as an oil.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. washwas washed with DCM
  3. washThe organic phase was washed with water
  4. dry with materialwas dried over MgSO4
  5. filtrationwas filtered
  6. concentrationwas concentrated under reduced pressure
  7. customThe crude mixture was purified by flash chromatography over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-9aa6d61415754e028475a30de29149ec
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08513252B2

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