Cesium carbonate → Tert-Butyl 4-[2-(4-methanesulfonylbenzoylamino)-pyridin-5-yl]-3,6-dihydro-2H-pyridine-1-carboxylate

HRID 42138

反応式

HRID 42138 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[N:6][CH:7]=1.CC1(C)C(C)(C)OB([C:29]2[CH2:30][CH2:31][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:33][CH:34]=2)O1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.O.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[CH3:19][S:16]([C:13]1[CH:14]=[CH:15][C:10]([C:9]([NH:8][C:5]2[CH:4]=[CH:3][C:2]([C:29]3[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH:30]=3)=[CH:7][N:6]=2)=[O:20])=[CH:11][CH:12]=1)(=[O:18])=[O:17]

参加物

7

反応物 3

HCID 10796Cesium carbonateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 60650971N-(5-Bromopyridin-2-yl)-4-methanesulfonylbenzamide

生成物 1

HCID 67083258Tert-Butyl 4-[2-(4-methanesulfonylbenzoylamino)-pyridin-5-yl]-3,6-dihydro-2H-pyridine-1-carboxylate収率 22.4%

試薬・触媒・溶媒 3

HCID 178477754HCID 178477754、化合物触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

To a solution of N-(5-bromopyridin-2-yl)-4-methanesulfonylbenzamide (287 mg, 0.81 mmol) and tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylate (305 mg, 0.97 mmol) in dry N,N-dimethylformamide (10 mL) was added [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (complex with dichloromethane) (33 mg, 0.040 mmol) and cesium carbonate (527 mg, 1.6 mmol). The mixture was stirred at 90° C. overnight under N2, allowed to cool to room temperature, diluted with water (10 mL) and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2) to give the title compound as a white crystal (83 mg, yield 22%).

後処理

  1. temperatureto cool to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2)

出典と根拠

ORDレコード
ord-f4e9a30a2210477b8a0084f312a4c427
出典データセット
uspto-grants-2013_09
特許番号
US08536176B2

関連ノート

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