Cesium fluoride → 2',6'-Bis(2,2,6,6-tetramethylpiperidin-1-yl)-2,3'-bipyridine

HRID 1779137ノート

反応式

HRID 1779137 の反応式
Br[C:2]1[C:3]([N:18]2[C:23]([CH3:25])([CH3:24])[CH2:22][CH2:21][CH2:20][C:19]2([CH3:27])[CH3:26])=[N:4][C:5]([N:8]2[C:13]([CH3:15])([CH3:14])[CH2:12][CH2:11][CH2:10][C:9]2([CH3:17])[CH3:16])=[CH:6][CH:7]=1.C([Sn](CCCC)(CCCC)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=1)CCC.[F-].[Cs+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:27][C:19]1([CH3:26])[CH2:20][CH2:21][CH2:22][C:23]([CH3:25])([CH3:24])[N:18]1[C:3]1[C:2]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=2)=[CH:7][CH:6]=[C:5]([N:8]2[C:9]([CH3:16])([CH3:17])[CH2:10][CH2:11][CH2:12][C:13]2([CH3:15])[CH3:14])[N:4]=1

参加物

6

反応物 3

HCID 25953Cesium fluorideHCID 6077842-(Tributylstannyl)pyridineHCID 676092893-Bromo-2,6-bis(2,2,6,6-tetramethylpiperidin-1-yl)pyridine

生成物 1

HCID 678921422',6'-Bis(2,2,6,6-tetramethylpiperidin-1-yl)-2,3'-bipyridine

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

実験手順

A mixture of 3-Bromo-2,6-bis(2,2,6,6-tetramethylpiperidin-1-yl)pyridine (0.4 g, 0.92 mmol), 2-(tributylstannyl)pyridine (0.4 g, 1.10 mmol), Pd(PPh3)4 (0.053 g, 0.046 mmol), and Cesium fluoride (0.28 g, 1.83 mmol) in Toluene (30 ml) was stirred under reflux for 2 days. After cooling down to room temperature the reaction was quenched with saturated CsF aqueous solution (100 mL). The product was extracted with ethylacetate. The product was purified by column chromatography on silica gel and obtained as white solide (Rf=0.5 in Ethylacetate:hexane=1:4, Yield=50 mg (12.5%))

後処理

  1. temperatureunder reflux for 2 days
  2. customwas quenched with saturated CsF aqueous solution (100 mL)
  3. extractionThe product was extracted with ethylacetate
  4. customThe product was purified by column chromatography on silica gel
  5. customobtained as white solide (Rf=0.5 in Ethylacetate:hexane=1:4, Yield=50 mg (12.5%))

出典と根拠

ORDレコード
ord-f26caf7e0acf4eb181c046c258d077f3
出典データセット
uspto-grants-2016_02
特許番号
US09269912B2

反応ノート

読み込み中…