Cesium fluoride → 1-[2-[4-[[6-Methoxy-2-(5-methylsulfonyl-3-thienyl)-1-naphthyl]oxy]phenoxy]ethyl]piperidine

HRID 445223노트

반응식

HRID 445223 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:16][CH:15]=1)=[C:8](OS(C(F)(F)F)(=O)=O)[CH:7]=[CH:6]2.C[Sn](C)(C)[C:39]1[CH:43]=[C:42]([S:44]([CH3:47])(=[O:46])=[O:45])[S:41][CH:40]=1.[F-].[Cs+]>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:16][CH:15]=1)=[C:8]([C:39]1[CH:43]=[C:42]([S:44]([CH3:47])(=[O:46])=[O:45])[S:41][CH:40]=1)[CH:7]=[CH:6]2

참가 물질

7

반응물 3

HCID 25953Cesium fluorideHCID 116133766-Methoxy-1-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)naphthalen-2-yl trifluoromethanesulfonateHCID 58338539Trimethyl-(5-methylsulfonyl-3-thienyl)stannane

생성물 1

HCID 583385611-[2-[4-[[6-Methoxy-2-(5-methylsulfonyl-3-thienyl)-1-naphthyl]oxy]phenoxy]ethyl]piperidine수율 57.9%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 167845palladium(II) acetate촉매HCID 6342Acetonitrile용매2회

반응 조건

온도
90 °C

실험 절차

Combine palladium(II)acetate (0.043 g 0.19 mmol) and trycyclohexylphosphine (0.081 g, 0.29 mmol) in acetonitrile (15 mL) and sonicate for 10 minutes. Add [6-methoxy-1-[4-[2-(1-piperidyl)ethoxy]phenoxy]-2-naphthyl]trifluoromethanesulfonate (0.5 g, 0.95 mmol), trimethyl-(5-methylsulfonyl-3-thienyl)stannane (0.94 g, 2.9 mmol) and palladium mixture to a suspension of cesium fluoride (0.5 g, 3.3 mmol) in acetonitrile (40 mL). Warm the resulting mixture to 90° C. and stir for 18 hours. Cool the mixture to room temperature and concentrate. Partition the resulting residue between ethylacetate and saturated aqueous sodium bicarbonate. Separate the layers and wash the organic layer with saturated aqueous ammonium chloride and brine, then dry with sodium sulfate. Concentrate the resulting solution and purify by flash chromatography (0-5% methanol in dichloromethane) to obtain the title compound (0.3 g, 0.55 mmol).

후처리

  1. customsonicate for 10 minutes
  2. temperatureCool the mixture to room temperature
  3. concentrationconcentrate
  4. customPartition the resulting residue between ethylacetate and saturated aqueous sodium bicarbonate
  5. customSeparate the layers
  6. washwash the organic layer with saturated aqueous ammonium chloride and brine
  7. dry with materialdry with sodium sulfate
  8. concentrationConcentrate the resulting solution
  9. custompurify by flash chromatography (0-5% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-0deb72a22e974dd38dda7abf22a2a45f
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476300B2

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