Cesium carbonate → (2-(2H-1,2,3-Triazol-2-YL)phenyl)methanol

HRID 41582

反応式

HRID 41582 の反応式
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][OH:9].[NH:10]1[CH:14]=[CH:13][N:12]=[N:11]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.[Cu]I.CN[C@@H]1CCCC[C@H]1NC>[N:10]1[N:11]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH2:8][OH:9])[N:12]=[CH:13][CH:14]=1

参加物

7

反応物 3

HCID 10796Cesium carbonateHCID 1076292-Iodobenzylic alcoholHCID 178418936HCID 178418936、化合物

生成物 1

HCID 67251671(2-(2H-1,2,3-Triazol-2-YL)phenyl)methanol収率 130%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamine触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
160 °C

実験手順

To a mixture of (2-iodophenyl)methanol [5159-41-1] (1.50 g, 6.41 mmol), 1H-1,2,3-triazole (0.797 g, 11.54 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine [68737-65-5] (0.091 g, 0.641 mmol) and Cs2CO3 (3.76 g, 11.54 mmol) in DMF (15 mL), CuI (0.61 g, 3.20 mmol) was added and the reaction mixture was stirred for 20 min at 120° C. and 15 min at 160° C. in the microwave. The reaction mixture was cooled to rt and filtered to remove the solids. The filtrate was concentrated under reduced pressure. The residue was purified by flash-column chromatography over silicagel (eluent: gradient 10%-100% ethyl acetate/heptane) to yield the title compound (1.46 g, 64%). [1H NMR (400 MHz, DMSO-d6) ♀ ppm 8.10 (s, 2H), 7.74 (d, J=7.53 Hz, 1H), 7.61 (dd, J=8.03, 1.25 Hz, 1H), 7.52 (td, J=7.53, 1.25 Hz, 1H), 7.44 (m, 1H), 5.26 (t, J=5.40 Hz, 1H), 4.59 (d, J=5.02 Hz, 2H); LCMS RtA=0.68, [M+H]+=176.1].

後処理

  1. additionwas added
  2. temperatureThe reaction mixture was cooled to rt
  3. filtrationfiltered
  4. customto remove the solids
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by flash-column chromatography over silicagel (eluent: gradient 10%-100% ethyl acetate/heptane)

出典と根拠

ORDレコード
ord-e73e2ef4f7bb44c99e97196b1224ac4c
出典データセット
uspto-grants-2013_09
特許番号
US08530648B2

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