Diisopropylethylamine → ethyl 2-(1-(2,2-difluoro-2-phenylethyl)-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxylate

HRID 2381863Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2381863
[C:1]([C:3]1[S:4][C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:6]([CH3:8])[N:7]=1)#[CH:2].[N:14]([CH2:17][C:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([F:20])[F:19])=[N+:15]=[N-:16].C(N(CC)C(C)C)(C)C>O1CCCC1.[Cu]I>[F:19][C:18]([F:20])([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH2:17][N:14]1[CH:2]=[C:1]([C:3]2[S:4][C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:6]([CH3:8])[N:7]=2)[N:16]=[N:15]1

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 57656188(2-Azido-1,1-difluoroethyl)benzeneHCID 59179676Ethyl 2-ethynyl-4-methylthiazole-5-carboxylate

Produkt 1

HCID 59179655ethyl 2-(1-(2,2-difluoro-2-phenylethyl)-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxylateAusbeute 67,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a degassed solution of ethyl 2-ethynyl-4-methylthiazole-5-carboxylate (0.10 g, 0.51 mmol) and (2-azido-1,1-difluoroethyl)benzene (0.14 g, 0.77 mmol) in tetrahydrofuran (5 mL) was added N,N-diisopropylethylamine (0.10 mL, 0.61 mmol), and copper(I) iodide (0.002 g, 0.01 mmol). The reaction mixture was stirred at ambient temperature under nitrogen for 17 hours, and concentrated in vacuo. The residue was purified by column chromatography to afford the title compound as a white solid (0.13 g, 67%): 1H NMR (300 MHz, CDCl3) δ 8.24 (s, 1H), 7.45-7.31 (m, 5H), 5.02-4.93 (m, 2H), 4.20 (q, J=7.1 Hz, 2H), 2.65 (s, 3H), 1.33 (t, J=7.1 Hz, 3H); MS (ES+) m/z 379.3 (M+1).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fc6125bc9d9f4520a658b305c43c8909
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08258160B2

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