Dimethyl Sulfoxide → HCID 58466470, 화합물

HRID 2092328노트

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HRID 2092328 반응식
Cl[C:2]1[C:11]2[C:6](=[C:7]([I:13])[C:8]([CH3:12])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[F:14][C:15]([F:24])([F:23])[C:16]1[CH:17]=[C:18]([OH:22])[CH:19]=[CH:20][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CS(C)=O>O.C(OCC)(=O)C>[I:13][C:7]1[C:8]([CH3:12])=[CH:9][CH:10]=[C:11]2[C:6]=1[CH:5]=[CH:4][N:3]=[C:2]2[O:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([C:15]([F:14])([F:23])[F:24])[CH:17]=1

참가 물질

7

반응물 4

HCID 679Dimethyl SulfoxideHCID 73763-(Trifluoromethyl)phenolHCID 10796Cesium carbonateHCID 58466468HCID 58466468, 화합물

생성물 1

HCID 58466470HCID 58466470, 화합물수율 73.6%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

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온도
170 °C

실험 절차

1-Chloro-5-iodo-6-methylisoquinoline (0.250 g, 0.824 mmol), 3-(trifluoromethyl)phenol (0.200 g, 1.24 mmol), cesium carbonate (0.590 g, 1.81 mmol) were all placed in a clear microwave vial along with 3 ml of DMSO. The vial was capped and heated in a Personal Chemistry SmithSynthesizer to 170° C. for 20 minutes. The reaction was diluted with water and ethyl acetate. The organic layer washed (2×) with an aqueous saturated solution of sodium bicarbonate, then with water and then brine. The organic layer was then dried with sodium sulfate and purified by column chromatography on silica gel using a gradient of 60-100% EtOAc in hexanes to give 5-iodo-6-methyl-1-(3-(trifluoromethyl)phenoxy)isoquinoline (0.260 g, 73.6% yield) as a white solid. MS(M+H)+ 430.

후처리

  1. customThe vial was capped
  2. washThe organic layer washed (2×) with an aqueous saturated solution of sodium bicarbonate
  3. dry with materialThe organic layer was then dried with sodium sulfate
  4. custompurified by column chromatography on silica gel using a gradient of 60-100% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-521c38c145c74ed5b9f9f170106f1c75
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08440674B2

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