5-(Methylsulfonyl)-1H-indole → tert-butyl 4-((6-(5-(methylsulfonyl)-1H-indol-1-yl)pyridin-3-yl)oxy)piperidine-1-carboxylate

HRID 1468014

反応式

HRID 1468014 の反応式
Cl[C:2]1[N:7]=[CH:6][C:5]([O:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O-:17])=[O:16])[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[CH3:18][S:19]([C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[NH:27][CH:26]=[CH:25]2)(=[O:21])=[O:20].[CH3:31][C:32]([O-])([CH3:34])[CH3:33].[Na+]>O1CCOCC1.CC(O)=O.CC(P(C(C)(C)C)C1C(C2[C-]=CC=CC=2)=CC=CC=1)(C)C.[Pd]>[CH3:18][S:19]([C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[N:27]([C:2]1[N:7]=[CH:6][C:5]([O:8][CH:9]3[CH2:14][CH2:13][N:12]([C:15]([O:17][C:32]([CH3:34])([CH3:33])[CH3:31])=[O:16])[CH2:11][CH2:10]3)=[CH:4][CH:3]=1)[CH:26]=[CH:25]2)(=[O:21])=[O:20]

参加物

6

反応物 3

HCID 149732305-(Methylsulfonyl)-1H-indoleHCID 23676156Sodium t-butoxideHCID 866961924-((6-Chloropyridin-3-yl)oxy)piperidine-1-carboxylate

生成物 1

HCID 67805679tert-butyl 4-((6-(5-(methylsulfonyl)-1H-indol-1-yl)pyridin-3-yl)oxy)piperidine-1-carboxylate収率 74.4%

試薬・触媒・溶媒 2

HCID 119822622-(2'-Di-tert-butylphosphine)biphenylpalladium(II) acetate触媒HCID 312751,4-Dioxane溶媒

実験手順

To a mixture of 4-((6-chloropyridin-3-yl)oxy)piperidine-1-carboxylate (intermediate-6) (0.440 g, 1.4 mmol) and 5-(methylsulfonyl)-1H-indole (intermediate-21) (0.261 g, 1.3 mmol) in anhydrous dioxane (5 mL), 2-(2′-Di-tert-butylphosphine) biphenylpalladium(II)acetate (0.130 g, 0.281 mmol) and NaOtBu (sodium tert.butoxide) (0.312 g, 0.960 mmol) were added. The resultant reaction mixture was refluxed for 4-5 h. The reaction mixture was filtered over celite and filtrate was concentrated in vacuo. The residue was purified by flash column chromatography to give tert-butyl 4-((6-(5-(methylsulfonyl)-1H-indol-1-yl)pyridin-3-yl)oxy)piperidine-1-carboxylate (0.337 g, 50%).

後処理

  1. additionwere added
  2. customThe resultant reaction mixture
  3. temperaturewas refluxed for 4-5 h
  4. filtrationThe reaction mixture was filtered over celite and filtrate
  5. concentrationwas concentrated in vacuo
  6. customThe residue was purified by flash column chromatography

出典と根拠

ORDレコード
ord-f3480cbd231c4f45a147bb0ac3d2f12e
出典データセット
uspto-grants-2015_04
特許番号
US09000175B2

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