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

HRID 41582

반응식

HRID 41582 반응식
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

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 1076292-Iodobenzylic alcoholHCID 178418936HCID 178418936, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamine촉매HCID 6228Dimethylformamide용매

반응 조건

온도
160 °C

실험 절차

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].

후처리

  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)

출처 및 근거

ORD 기록
ord-e73e2ef4f7bb44c99e97196b1224ac4c
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530648B2

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