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

HRID 2381863ノート

反応式

HRID 2381863 の反応式
[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

参加物

6

反応物 3

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

生成物 1

HCID 59179655ethyl 2-(1-(2,2-difluoro-2-phenylethyl)-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxylate収率 67.4%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-fc6125bc9d9f4520a658b305c43c8909
出典データセット
uspto-grants-2012_09
特許番号
US08258160B2

反応ノート

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