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

HRID 445223ノート

反応式

HRID 445223 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 167845palladium(II) acetate触媒HCID 6342Acetonitrile溶媒2 回

反応条件

温度
90 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-0deb72a22e974dd38dda7abf22a2a45f
出典データセット
uspto-grants-2013_07
特許番号
US08476300B2

反応ノート

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