Cesium carbonate → 2-Methoxy-4-((6-(trifluoromethyl)pyridin-3-yl)methoxy)pyridine

HRID 469686

반응식

HRID 469686 반응식
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][CH3:9])[CH:3]=1.[F:10][C:11]([F:21])([F:20])[C:12]1[N:17]=[CH:16][C:15]([CH2:18][OH:19])=[CH:14][CH:13]=1.CC1C=NC2C(C=1C)=CC=C1C=2N=CC(C)=C1C.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.[Cu]I>[CH3:9][O:8][C:4]1[CH:3]=[C:2]([O:19][CH2:18][C:15]2[CH:16]=[N:17][C:12]([C:11]([F:21])([F:10])[F:20])=[CH:13][CH:14]=2)[CH:7]=[CH:6][N:5]=1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 742653,4,7,8-Tetramethyl-1,10-phenanthrolineHCID 36138956-(Trifluoromethyl)pyridine-3-methanolHCID 140623094-Bromo-2-methoxypyridine

생성물 1

HCID 575147592-Methoxy-4-((6-(trifluoromethyl)pyridin-3-yl)methoxy)pyridine수율 72.4%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 1140Toluene용매

실험 절차

4-Bromo-2-methoxypyridine (3.06 g, 16.2 mmol), (6-(trifluoromethyl)pyridin-3-yl)methanol (2.74 g, 15.5 mmol), 3,4,7,8-tetramethylphenanthroline (0.36 g, 0.15 mmol), CuI (0.14 g, 0.74 mmol) and Cs2CO3 (7.57 g, 23.2 mmol) were combined in toluene (15 mL) and heated to reflux under a nitrogen atmosphere for 16 h. Upon cooling the mixture was purified by flash column chromatography (silica gel, hexanes/EtOAc, 1:0 to 1:1) to provide the title compound (3.19 g, 72%) as a red oil: 1H NMR (300 MHz, CDCl3) δ 8.78 (s, 1H), 8.02 (d, J=5.9 Hz, 1H), 7.95 (d, J=8.1 Hz, 1H), 7.32 (d, J=8.0 Hz, 1H), 6.55 (dd, J=5.9, 2.2 Hz, 1H), 6.26 (d, J=2.2 Hz, 1H), 5.16 (s, 2H), 3.93 (s, 3H).

후처리

  1. temperatureheated
  2. temperatureto reflux under a nitrogen atmosphere for 16 h
  3. temperatureUpon cooling the mixture
  4. customwas purified by flash column chromatography (silica gel, hexanes/EtOAc, 1:0 to 1:1)

출처 및 근거

ORD 기록
ord-809c143a485b4ac1bf415fd6424c117e
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629158B2

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