Cesium carbonate → 4-(3-Methyl-5-nitropyridin-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylic acid tert-butyl ester

HRID 1748588ノート

反応式

HRID 1748588 の反応式
Br[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:18]([O:22][C:23]([N:25]1[CH2:30][CH:29]=[C:28](B2OC(C)(C)C(C)(C)O2)[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19]>O1CCOCC1.O>[C:18]([O:22][C:23]([N:25]1[CH2:26][CH:27]=[C:28]([C:2]2[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=2)[CH2:29][CH2:30]1)=[O:24])([CH3:21])([CH3:19])[CH3:20]

参加物

6

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 52004662-Bromo-3-methyl-5-nitropyridine

生成物 1

HCID 866925414-(3-Methyl-5-nitropyridin-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylic acid tert-butyl ester収率 90%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

A mixture of 2-bromo-3-methyl-5-nitropyridine (10.0 g), cesium carbonate (42 g), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II)dichloridedichloromethane complex (1.88 g), and N-tert-butyloxycarbonyl-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester (15 g) in 1,4-dioxane (150 ml) and water (50 ml) was stirred at 110° C. for 2.5 hours. To the reaction solution was added water, extracted with chloroform, the organic layer was washed with water, dried over anhydrous sodium sulfate, and then the solvent was evaporated in vacuo. The obtained solid was washed with a mixed solution of n-hexane and ethyl acetate to give 4-(3-methyl-5-nitropyridin-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylic acid tert-butyl ester (13.25 g) as a red solid.

後処理

  1. extractionextracted with chloroform
  2. washthe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated in vacuo
  5. washThe obtained solid was washed with a mixed solution of n-hexane and ethyl acetate

出典と根拠

ORDレコード
ord-0ed2bf4eb903499fbbbb8183a6785f4a
出典データセット
uspto-grants-2015_10
特許番号
US09150555B2

反応ノート

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