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Methyl iodide → 3-[Methoxy(Phenyl)Methyl]-4-Phenyl-8-(Trifluoromethyl)Quinoline

HRID 2104493
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HRID 2104493 반응식
[C:1]1([CH:7]([C:9]2[CH:10]=[N:11][C:12]3[C:17]([C:18]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:16][CH:15]=[CH:14][C:13]=3[C:25]([F:28])([F:27])[F:26])[OH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].I[CH3:32]>CN(C=O)C>[CH3:32][O:8][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[CH:16][CH:15]=[CH:14][C:13]=2[C:25]([F:28])([F:26])[F:27]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11222693Phenyl[4-Phenyl-8-(Trifluoromethyl)Quinolin-3-yl]Methanol

생성물 1

HCID 669142423-[Methoxy(Phenyl)Methyl]-4-Phenyl-8-(Trifluoromethyl)Quinoline수율 75.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Phenyl[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]methanol (Example 34, 0.05 g, 0.132 mmol) was taken into DMF (3 mL). Next, NaH (0.011 g, 0.264 mmol, 60% dispersion) was added and stirred for 1 hour at room temperature. Next, iodomethane (0.04 ml, 0.66 mmol) was added and allowed to stir for 30 minutes. The reaction was quenched with water then extracted with ether. The combined organics were dried over magnesium sulfate and concentrated. The resulting material was purified via column chromatography using 5% ethyl acetate in hexane as the eluent to yield 0.039 g (75%) of desired product as a white solid. MS (ESI) m/z 394 ([M+H]+); Anal. Calcd for C24H18F3NO: C, 73.27; H, 4.61; N, 3.56. Found: C, 73.15; H, 4.16; N, 3.41.

후처리

  1. stirringto stir for 30 minutes
  2. customThe reaction was quenched with water
  3. extractionthen extracted with ether
  4. dry with materialThe combined organics were dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe resulting material was purified via column chromatography

출처 및 근거

ORD 기록
ord-8db5721831b247498a55bbdbac0508ed
출처 데이터셋
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07576215B2

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